Senior Property Accountant
North York, ON – hybrid
$60,000-$95,000 base plus benefits (part-time vs full-time)

The Senior Property Accountant is responsible for the full-cycle real estate accounting and the generation of timely, accurate financial reports for the real estate assets. This role supports internal decision-making through detailed analysis of actual results and management of the monthly close cycle. This is a position requiring a hands-on professional capable of collaborating across the team to provide critical financial insights. The company is very open to having this person work remotely, hybrid, or in the office and this can be a part-time or full-time position. Minimal training will be provided. Ideally, we would like to find someone who has used MS 365 Business Central (Navision).

Responsibilities

• Financial Accounting & Reporting: Manage the full monthly close cycle, including the preparation of month-end entries, bank reconciliations, HST returns, and general ledger maintenance.

• Asset Management Support: Handle accounting for asset acquisitions and dispositions, including proration adjustments, reconciliations, and accounting for closing statements.

• Accounts Receivable & Payable: Actively monitor AR and manage AP processes to ensure accurate expense coding and timely collections.

• Audit & Compliance: Support annual audits by preparing schedules and documentation with high attention to detail.

• Capital & Project Accounting: Track capital project costs, maintain capital asset continuity schedules, and process monthly depreciation and accruals.

• Process Improvement: Identify opportunities to improve workflows and shorten the month-end close process to provide stakeholders with faster financial information.

Qualifications & Experience

• Experience: Minimum of 8-10+ years of full-cycle real estate or commercial property accounting experience.

• Technical Proficiency: Hands-on experience with Business Central or Navision is required.

• Education: Bachelor’s degree in Business Administration, Commerce, or a related field. (Note: Experienced candidates without a CPA designation are encouraged to apply).

• Soft Skills: Strong analytical and communication skills, with a demonstrated ability to understand complex financial concepts and "connect the dots".

Work Arrangement & Compensation

• Flexible Environment: We are open to remote work arrangements or a part-time schedule with designated days in the office in North York, ON.

• Salary Range: $65,000 – $95,000 per year (commensurate with experience and work arrangement).

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Associate – Acquisitions and Asset Management

North York, Ontario - onsite

$100,000-$120,000 base plus 15% bonus

This company is a fast-growing real estate company in North York. You will get experience and insight into the multifaceted operations and execution of high-profile real estate development projects and income-producing property portfolios. The company is looking to add a new person as an Associate of Acquisitions / Asset Management.

You will be responsible for the day to day duties of managing real estate models, acquisitions, monitoring project performance, planning/analyzing budgets, asset management, presentations, corporate analysis and identifying investment opportunities. If this new position sounds like a fit for you, do not hesitate to apply.

Responsibilities:

• Conduct due diligence and feasibility studies to analyze acquisitions

• Technical analysis and ensure proper accounting for acquisitions and deal disposition

• Underwrite new development deals and create intricate proforma budgets

• Conduct project budget review with focus on actual vs budget proformas monthly to meet company and project objectives

• Analyze project cash flows and prepare sensitivity analysis to study impacts on overall project

• Prepare equity and investment IRR waterfall analysis to ensure KPI’s are met

• Continuously Monitor and update all project proformas, cashflows and IRR models in conjunction with project accountants, controller, and CFO

• Create monthly project financial reports to present to LP partners, CEO, CFO and COO.

• Participate, collaborate and give recommendations on projects and identify efficiencies for continuous improvements

• Assist with execution of development portfolio strategy related to investments and supporting executive team on execution of transactional activity

Requirements:

• A minimum of two (2) years’ experience in financial/investment analysis in real estate development

• Completed a university degree

• Excellent communication (both written and verbal) and presentation skills

• Strong process management/improvement skills with a mindset for continuous improvement

• Proficient in Microsoft Office suite some modeling software (Word, Excel, Project, Outlook)

If you are interested in learning more about this opportunity, please apply now or email your resume in confidence to angie@winchesters.ca. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Director of Debt Finance

Calgary, AB (5 Days In-Office)

Competitive base salary plus unparalleled bonus and benefits package

We are partnered with a leading, publicly traded real estate company in Calgary to identify their next Director of Debt Finance. You will take ownership of the organization's overarching capital strategy, steering complex financing executions and managing enterprise liquidity. Operating on-site five days a week, this is a highly visible leadership role where you will act as the primary interface with lenders, appraisers, and key institutional stakeholders. You will also deal directly with the CEO and CFO.

Responsibilities:

• Lead the sourcing, structuring, and execution of complex debt financing, including conventional term debt and CMHC-insured loans. 

• Optimize loan sizing across a massive national portfolio while balancing the overall cost of capital and financing expenses. 

• Actively manage the debt maturity ladder, evaluating renewal versus refinance scenarios while monitoring market conditions, rate outlooks, and spread movements. 

• Oversee the management of the enterprise mortgage portfolio, driving the compliance, initiation, and renewal processes. 

• Manage complex application processes and relationships with CMHC, maintaining a deep understanding of evolving CMHC policies. 

• Engage and oversee third-party reporting (Appraisals, BCA, ESA, and QS reports) and lead annual loan review processes with both lenders and CMHC. 

• Oversee the corporate liquidity position, driving cash forecasting and working capital optimization. 

• Manage credit facilities and borrowing base availability, ensuring the platform has sufficient liquidity to execute development pipelines, CAPEX programs, and distributions. 

• Monitor credit facility covenants and generate strict quarterly compliance certificates. 

• Manage periodic daily treasury functions, including wire transfers, EFTs, and bank transfers. 

What You Bring

• An undergraduate degree in Commerce, Finance, Economics, or a related field (a CFA, CPA, or MBA is highly preferred). 

• Extensive experience in real estate finance, capital markets, or treasury

• A proven track record of successfully closing complex financings and executing strong negotiations with lenders and counterparties. 

• The ability to think strategically about portfolio-level capital optimization, supported by a strong macro-economic awareness. 

• Exceptional executive communication skills and familiarity with modern treasury management systems. 

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Real Estate Associate

Toronto, ON (In Office)

$95,000 – $110,000 base + bonus

We’re working with a well-established real estate investment and development firm seeking an Investment & Development Analyst to join their team.

This role offers strong exposure to acquisitions, development, and asset management across a diversified portfolio. You’ll work closely with senior leadership on evaluating new opportunities and supporting active projects.

Key Responsibilities

• Build financial models for acquisitions, developments, and redevelopments

• Conduct underwriting, valuation, and sensitivity analysis

• Support due diligence including review of leases, financials, and operating data

• Assist in sourcing opportunities and maintaining broker relationships

• Track market activity (sales, leasing trends, comps)

• Support development projects and coordinate with internal teams and consultants

• Prepare investment memos, reports, and presentations

Key Requirements

• 3+ years in real estate investment, development, or acquisitions

• Strong financial modeling skills (Excel)

• Experience with Argus and/or Yardi is an asset

• Solid understanding of real estate fundamentals

Additional Details

• 5 days onsite

• High-growth exposure working directly with leadership

We thank all applicants for their interest; however, only those selected for an interview will be contacted.

Accounts Payable & Systems Administrator (NEWSTAR)

Norh York, ON - onsite

$75,000-$95,000 base plus bonus

Role Summary

We are seeking a detail-oriented professional to manage full-cycle Accounts Payable while serving as the primary NEWSTAR Enterprise System Administrator. This is a hybrid role designed for someone who loves the logic of accounting but also enjoys the technical side of managing an ERP system. You will ensure vendors are paid accurately while optimizing the NEWSTAR environment to improve financial reporting and workflow efficiency.

Responsibilities:

I. Accounts Payable Operations (The "Accounting" Side)

• Full-Cycle AP: Manage high-volume invoice entry, ensuring accurate GL coding and 3-way matching (Invoice/PO/Receiver).

• Subcontractor Management: Handle complex construction accounting tasks, including holdbacks (retention), insurance compliance verification, and WCB/WSIB clearances.

• Payment Execution: Prepare and execute weekly EFT/ACH runs and cheque payments within NEWSTAR.

• Reconciliations: Perform monthly vendor statement reconciliations and assist with month-end closing activities.

• Inquiry Resolution: Act as the primary point of contact for vendor billing discrepancies and internal department inquiries.

II. NEWSTAR Systems Administration (The "Admin" Side)

• User Management: Set up and maintain user profiles, security roles, and permission levels within NEWSTAR.

• Workflow Optimization: Monitor and troubleshoot automated AP workflows; identify areas to streamline data entry or reporting.

• Data Integrity: Perform regular audits of the vendor master file and job cost codes to ensure data consistency.

• Report Generation: Build and maintain custom financial reports using the NEWSTAR Report Writer and Excel integrations.

• System Liaison: Act as the internal "help desk" for other staff members and serve as the main point of contact for Constellation HomeBuilder Systems (NEWSTAR) technical support.

Requirements:

• Experience: 3+ years in Accounts Payable, specifically within the residential construction or land development industry.

• Software Expertise: Direct experience with NEWSTAR Enterprise (Constellation HomeBuilder Systems) is highly preferred.

• Technical Aptitude: Advanced proficiency in Microsoft Excel (Pivot Tables, VLOOKUPs). Comfortable learning the "back-end" of accounting software.

• Industry Knowledge: Understanding of construction-specific accounting (Job Costing, Commitments, Change Orders, and Lien Waivers).

• Attention to Detail: Ability to spot a coding error or a system glitch that others might miss.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Director of CMHC Mortgage Servicing

Toronto, Ontario – Downtown

$150,000-$200,000 base plus lucrative bonus and excellent benefits

Are you a commercial mortgage expert looking for an opportunity to build something new? We’re looking for a highly skilled professional to lead the development of a team dedicated to CMHC mortgage servicing. This is a chance to take ownership of a department from the ground up, driving innovation and efficiency while ensuring top-tier service.

If you thrive in a fast-paced, transparent environment and take pride in the quality of your work, this could be your next big role.

Requirements:

• Build and lead a new team focused on CMHC-insured mortgage servicing.

• Provide expert guidance on CMHC mortgage administration processes and best practices.

• Design and implement efficient mortgage servicing solutions, working closely with cross-functional teams.

• Ensure full compliance with CMHC and industry regulations.

• Develop training programs to enhance team expertise.

• Lead and mentor a high-performing team, fostering a collaborative culture.

• Oversee a growing portfolio of commercial CMHC-insured mortgages, ensuring smooth administration.

• Mortgage Servicing – Oversee payments, escrow management, and investor reporting.

• Identify and mitigate portfolio risks.

• Maintain strong relationships with borrowers and investors.

• Prepare and present reports on portfolio performance to senior leadership.

• Continuously refine processes to enhance efficiency and customer experience.

• Help shape team objectives and execute strategic plans.

Requirements:

• 5+ years of experience in CMHC mortgage administration, with a focus on process improvement and compliance.

• Proven ability to lead a team.

• Ideally deep expertise in CMHC mortgage regulations, policies, and industry standards.

• Strong process development skills with a track record of creating and optimizing workflows.

• Professional and trustworthy, capable of building strong relationships with internal teams and external partners.

• Strong written and verbal communication skills.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Associate Director of Originations, CMHC

Toronto, ON - onsite 

$140,000-$150,000 base plus uncapped commission

Our client is a Canadian private equity real estate firm seeking an Associate Director or Director of Originations to join their team in downtown Toronto, Ontario. This role will appeal to you if you possess a true sense of ownership, take great pride in your work quality, and are a problem solver at heart. This is an ideal opportunity for a professional ready to transition from back-office modeling to a high-impact, client-facing sales role.

Responsibilities

• Originate hundreds of millions of CMHC loans annually in primary and secondary markets across Canada. Open to individuals who use broker networks or direct.

• Assist the underwriting team with loan assessment, structuring, and closing due diligence.

• Ensure all loans conform to company and CMHC’s policies and procedures.

• Maintain a detailed pipeline.

• Attend various networking events outside of normal working hours. This must be an exciting aspect of the job for you.

Candidate Profile

• Minimum 5 years of related work experience - open to individuals coming from equity or debt sides.

• Undergraduate degree in business or related field

• Superior analytical and risk assessment skills.

• Excellent communication and interpersonal skills.

• Strong understanding of real estate underwriting guidelines (ideally multi-family).

• Self-starter with the ability to work independently and as part of a team.

• Strong attention to detail and ability to multitask in a fast-paced environment.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Director of Finance – Accounting

Downtown Toronto, ON – onsite 5 days per week

$145,000-$165,000 plus large bonus and excellent benefits

We’re seeking an experienced Director of Finance to join a dynamic Toronto-based client. This role is pivotal in overseeing the financial reporting processes – monthly, quarterly, and annually – for the team. You’ll support operations, including acquisitions and dispositions, and play an integral role in working cross-functionally with senior leadership, investment, asset management, and property finance teams.

Responsibilities:

• Lead monthly, quarterly, and annual reporting deliverables, ensuring accuracy, timeliness, and ASPE compliance for a portfolio of funds.

• Review and verify monthly forecasts to maintain compliance with covenants, manage liquidity, and provide accurate projections for acquisitions and dispositions.

• Oversee the quarterly board reporting process, ensuring all inputs are accurate for board presentations.

• Manage quarterly compliance reporting to lenders.

• Direct the annual budget process, validating the accuracy and reasonableness of all assumptions.

• Serve as the primary point of contact for the annual audit.

• Oversee investor transactions, including capital calls, returns, preferred returns, and gain distributions.

• Address investor inquiries promptly and professionally.

• Lead and mentor a team of four, providing guidance and fostering professional growth.

Requirements:

• Undergraduate degree in Finance or Business; CPA designation required.

• Real estate experience is a major plus.

• 8+ years of experience

• Supervisory experience

• Strong written and verbal communication abilities.

• Preference will be given to individuals with prior audit firm experience

• A collaborative team player with high ethical standards and integrity.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Regional Finance Director

Fully remote

$140,000-$160,000 base plus bonus and excellent benefits

Our client is in growth mode and is looking to find a Regional Finance Director. Step into a high-impact role as a hands-on Finance Director, owning the financial function from daily accounting to strategic planning. Reporting to the CFO and collaborating with the Senior Leadership Team, you will help with setting up new controls, processes and procedures. We are looking for someone who is hungry to grow and is comfortable putting numbers into a story for senior management.

Responsibilities

• Core Accounting Operations

• FP&A and Strategic Analysis

• Reporting and Data Optimization

• Compliance and Risk Management

Requirements:

• CPA and university degree.

• 10 years of progressive experience in accounting or finance.

• Strong FP&A experience

• Excellent communication skills - both oral and written

We appreciate all interest in this opportunity; however, only candidates selected for an interview will be contacted.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Analyst – Acquisitions and Asset Management

Toronto, ON - hybrid

$75K-$85K base plus bonus

With this company being one of the fastest growing real estate consulting firms in the Greater Toronto Area,you will get experience and insight into the multifaceted operations and execution of high-profile real estate development projects and income-producing property portfolios in Canada and the US. The company is looking to add a new person as an Analyst of Acquisitions / Asset Management.

You will be responsible for the day to day duties of managing real estate models, acquisitions, monitoring project performance, planning/analyzing budgets, asset management, presentations, corporate analysis and identifying investment opportunities. If this new position sounds like a fit for you, do not hesitate to apply.

Responsibilities:

• Conduct due diligence and feasibility studies to analyze acquisitions

• Technical analysis and ensure proper accounting for acquisitions and deal disposition

• Underwrite new development deals and create intricate proforma budgets

• Conduct project budget review with focus on actual vs budget proformas monthly to meet company and project objectives

• Analyze project cash flows and prepare sensitivity analysis to study impacts on overall project

• Prepare equity and investment IRR waterfall analysis to ensure KPI’s are met

• Continuously Monitor and update all project proformas, cashflows and IRR models in conjunction with project accountants, controller, and CFO

• Create monthly project financial reports to present to LP partners, CEO, CFO and COO.

• Participate, collaborate and give recommendations on projects and identify efficiencies for continuous improvements

• Assist with execution of development portfolio strategy related to investments and supporting executive team on execution of transactional activity

Requirements:

• Must have at least 1-2+ years’ experience in financial/investment analysis in real estate

• Completed a university degree

• Are analytical and have ability to produce analysis in appropriate language and style

• Possess excellent communication (both written and verbal) and presentation skills

• Have ability to manage your time, with strong organizational skills and ability to prioritize tasks within a demanding environment

• Are proficient in Microsoft Office suite some modeling software (Word, Excel, Project, Outlook)

If you are interested in learning more about this opportunity, please apply now by sending your resume to eric@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Director, Investment Management (Real Estate)

$150,000 base + lucrative bonus 

4 weeks’ vacation | 4 days per week in office – Downtown Toronto

Our client, a leading platform for commercial real estate lending and investment located in Downtown Toronto, is recruiting for an entrepreneurial and strategic Director, Investment Management.

This is an outstanding opportunity for an investment professional with deep portfolio management and underwriting expertise who wants to play a hands-on role in driving fund performance, managing capital, and designing new investment vehicles across both debt and equity.

You will work closely with the SVP and the Capital Markets team to shape fund strategy, oversee credit risk, and scale new lending initiatives. You will also have a set on the investment committee and be instrumental in the strategic vision of this group.

The Role

In this role, you will provide portfolio oversight and performance analysis across multiple investment vehicles, balancing disciplined credit underwriting with innovative fund strategies. You will manage treasury functions, optimize capital deployment, and support ongoing fund reporting and investor communications.

A key part of this role involves building and scaling the firm’s newest lending program, designed to rapidly deploy capital into shorter-term, high-quality commercial real estate loans. Additionally, you will collaborate with leadership to structure and launch new investment vehicles, including potential Debt Funds, Equity Funds, or REITs.

Key Responsibilities

• Assist in treasury management across funds, optimizing capital deployment and liquidity.

• Conduct portfolio analysis, performance tracking, and risk rating for the total portfolio.

• Support ongoing fund reporting, investor communications, and compliance with investment policies.

• Evaluate commercial real estate loan opportunities and provide recommendations to Investment Committees.

• Review loan summaries, credit memos, and commitment letters.

• Lead outreach to broker and borrower networks to identify lending opportunities.

• Enhance policies, procedures, and reporting frameworks to strengthen credit governance.

• Collaborate with the SVP to structure and launch new investment vehicles (e.g., Senior Debt, Self-Storage, Apartment REITs).

• Work with legal counsel to structure and negotiate fund terms and investor agreements.

• Support the setup of new entities, fund operations, and reporting infrastructure.

Requirements:

• Undergraduate degree in business or finance

• 6+ years of experience in the commercial real estate industry (prior investment fund experience is an asset).

• Advanced proficiency in Excel, PowerPoint, and Word with the ability to distill complex data into clear insights.

• Strong ownership mindset with the confidence to engage investors and senior leadership.

• Entrepreneurial spirit with the ability to manage multiple priorities in a high-growth environment.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Accounts Payable Administrator (9-month contract position - potential for permanent)

Downtown, Toronto (4 days in office)

$55,000- $65,000 salary

Our client is a highly reputable property development and management company located in the heart of downtown Toronto (walking distance from Union). This role will report directly to the Manager, Accounting & Reporting and is an excellent opportunity to work in a fast paced, team environment. Please note that this role is a 9-month contract with potential to move to permanent, although it's not guaranteed. For this reason, we are giving preference to individuals who are not currently working and come from the real estate development industry. It is also worth noting that this role will include more than just Accounts Payable. It will also include accounting duties like bank reconciliations, HST filing, and more.

Responsibilities:

• Enter accurate and timely accounts payable invoices for each development project using established internal control practices.

• Process approved accounts payable invoices for payment.

• Maintain appropriate physical or electronic support for all accounts payable transactions.

• Create purchase orders in Excel for the development team and enter them into the Yardi system once approved.

• Input vendor invoices into the Yardi system weekly, ensuring correct legal entity and association with the appropriate contract, change order, or purchase order.

• Review vendor invoices for accuracy, including totals, taxes, billing entities, and matching them to purchase orders, contracts, and receiving reports.

• Verify vendor account status, respond to vendor inquiries, and ensure accounts are settled or outstanding balances are accurate.

• Follow up with vendors, development, and construction teams regarding monthly billing at month-end, ensuring all bills are received with correct supporting documentation.

• Assist with the development and implementation of new process improvement initiatives.

• Ensure all invoices entered are committed for payment in a timely manner and process cheques weekly.

• Ensure cheques have appropriate signatures.

• Determine the method of cheque delivery (mail, courier, or pick-up) in consultation with accountants.

• Ensure all bills are paid on time, and due dates are tracked appropriately.

• Update the vendor master list.

• Review the accounts payable aged listing monthly and follow up with accountants for any accounts payable over 30 days.

Requirements:

• 3-5 years of AP experience, preferably in real estate development

• Detail-oriented and organized

• Excellent communication skills

• Basic knowledge of Excel

If you would like to find out more about the role, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for an interview will be contacted.

If you are interested in learning more about this opportunity, please apply now by sending your resume to eric@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Financial Analyst - Financial Reporting 

Mississauga, ON - Fully hybrid

$90K-$95K base plus 10-15% bonus and excellent benefits

After decades of home building excellence, our client has earned a reputation as an award-winning developer and builder of master-planned communities. The organization is on a mission to be the most innovative community builder in Ontario. The environment here is dynamic, engaging, rewarding, and team-oriented. Reporting to the Controller, the Senior Financial Analyst (Financial Reporting) will support and manage all aspects of financial reporting to provide accurate information to internal and external stakeholders. This is a hands-on technical role responsible for the financial integrity of a complex corporate structure, including head office entities, holding companies, and over 60 project-level joint ventures.

Responsibilities:

• Complex Consolidations: Perform year-end and quarter-end closings for 3 corporate entities, 15 holding companies, and over 60 project-level joint ventures and limited partnerships.

• Financial Statements: Prepare and analyze financial statements on a quarterly and annual basis (Income Statement, Balance Sheet, Cash Flows, and Equity) in accordance with ASPE.

• Journal Entry Management: Interpret and analyze financial information posted to the GL. Post complex adjusting entries for fixed asset amortization, retained earnings allocation, holding company profit-sharing roll-ups, estimated costs to complete accruals, forfeited deposit income recognition, and WIP clean-up.

• Schedule Maintenance: Create and maintain detailed working papers and schedules, including fixed asset amortization, intercompany reconciliations, investment portfolio summaries, credit card reconciliations, and limited partners’ capital continuity (including preferred return calculations).

• Audit Management: Work closely with the company’s Auditor to finalize year-end financial statements. Prepare working papers using CaseWare for Compilation & Review Engagements and respond to external accounting firms’ inquiries.

• Tax Support: Assist in annual tax filings for all entities across the group. 

• Process Optimization: Clarify and standardize the internal closing process to streamline communication within the finance department. Create and maintain Standard Operating Procedures (SOPs) for financial reporting.

• Quality Assurance: Review, investigate, and correct errors and inconsistencies in financial entries, documents, and reports. This includes reviewing monthly bank reconciliations and HST filings prepared by bookkeepers to ensure accuracy.

• Ad Hoc Analysis: Research balance sheet items and income/expense fluctuations. Support the VP of Finance regarding capital calls, dividend and shareholder loan planning, funding deficiency analysis in profit-sharing partnerships, and dormant entity dissolvement.

Requirements:

• Education & Designation: CPA Designation preferred (working towards will be considered based on previous Public Accounting experience).

• Experience: Minimum 3 years of relevant experience, including experience working at a recognized CPA firm using CaseWare Working Papers.

• Software Proficiency: Proficient with Microsoft Suite (Word, Excel, Outlook, and PowerPoint).

• Soft Skills: Strong organizational skills with strong attention to detail and accuracy. Strong oral and written communication abilities are essential for liaising with external partners.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller

Oakville, ON - 30-32 hours per week or full-time

$115K-$125K base plus discretionary bonus, vacation and excellent benefits

A well-established real estate development and construction company in Oakville is hiring a Financial Controller to take on a key leadership role while the incumbent retires.

In this position, you’ll oversee both project-level and corporate accounting, lead monthly reporting processes, strengthen internal controls, support investor and lender reporting, and mentor one accountant. The role is ideal for someone who enjoys ownership, continuous improvement, and working closely with senior decision-makers in a company that has a very family feel. You will be given a lot of autonomy, you don't need to work full-time hours, and this business is the type of company that buys the team lunch every Friday and are sent home early at times. Most people at this company have been there for over ten years. This role reports to the President.

Key Responsibilities

• Oversee full-cycle accounting for 20+ entities

• Standardize and review monthly project reporting

• Approve month-end close and forecasts

• Review cost consultant reports and closing entries

• Prepare equity/debt draws and support investor relations

• Improve policies, processes, and accounting systems (may include a transition to Jonas Premier)

• Manage daily cash flow projections and trend reports

• Ad hoc responsibilities that you can take off the president

Ideal Candidate

• CPA designated

• 3+ years in an accounting leadership role

• Experience in real estate development

• Strong communication, Excel skills, and judgment

• Detail-oriented, organized, proactive, and team-focused

Please apply directly to this posting. Only shortlisted candidates will be contacted.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Accountant

Mississauga, ON – Onsite 

$85,000 – $95,000 base plus bonus

Our client is a very stable investment company based in Mississauga, Ontario. They are known for their supportive and positive culture, reasonable hours, and being an overall lovely place to work. While the role itself offers limited long-term growth, it provides stability, great work-life balance, and the chance to be part of a genuinely welcoming environment.

This Senior Accountant position will be responsible for full-cycle accounting across multiple entities, including management companies, project entities, and investor entities. The successful candidate will manage monthly accounting processes, financial reporting, and project accounting, as well as assist with year-end financials and external audits.

Responsibilities

• Maintain monthly accounting records, including AP, AR, bank reconciliations, and intercompany transactions

• Prepare and file HST returns

• Assist with cash management and planning

• Facilitate preparation of annual corporate tax returns with external auditors

• Support year-end financial statement preparation (experience required)

• Contribute to investor reporting and project accounting

• Assist with tax and financial audits

• Maintain complete and accurate supporting documentation

Requirements

• 5+ years of relevant accounting experience

• Strong EXCEL proficiency

• Solid understanding of ASPE

• Excellent organizational and communication skills

• Self-motivated, able to work under deadlines

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Accounts Payable Administrator

Remote with a few days per month in the Toronto office

$60,000-$70,000 plus vacation and excellent benefits plan

We are seeking a highly organized, detail-oriented, and resilient Accounts Payable Administrator to join a private family office. This is a foundational role that bridges the gap between rigorous financial record-keeping and seamless office operations.

The ideal candidate is someone who thrives in a smaller company environment and enjoys doing many different types of tasks. The position requires someone to be very hands-on with these duties and responsibilities.  We would like someone who isn’t just looking for a checklist; you are a problem-solver who takes full ownership of the process from start to finish. In this position you will handle office administration along with an array of accounting tasks like: AP, AR, bank reconciliations, and more. Many of the office administration tasks can be trained, but the client would like to find someone with at least some level of basic accounting experience (focus on payables). 

This role is going to be great for someone looking for a stable and secure place of work. If you’re looking for a ladder to climb, this will not be the right place for you. While you may expand on the duties you take on, the role will largely remain at this level with these responsibilities forever. 

Responsibilities

• Manage Accounts Payable (AP) and Accounts Receivable (AR), ensuring all entries are accurately coded in the accounting system (Xero).

• Execute bill payments via bank platforms and manage treasury functions, including inter-account transfers.

• Support month-end closures, perform bank and intercompany reconciliations, and prepare payment schedules/lists.

• Execute payroll cycles and organize tax slips and supporting documentation for year-end filings.

• Receive, file, and upload monthly investment and bank statements in accordance with established digital filing protocols.

• Support minute book maintenance, draft resolutions, and ensure the timely filing of corporate returns.

• Act as the point of contact for office operations, including managing contracts for security, IT/Internet, and property maintenance (e.g., snow removal, window washing).

• Serve as a professional point of contact for family members regarding payable matters and personal financial administration.

Requirements:

• Tech-Savvy: Proficient in MS 365 (advanced Excel) and ideally experienced with Xero.

• High level of discretion - You understand the high level of confidentiality required when working within a private family office.

• 5+ years of experience in accounting or office management; prior experience in a family office or private wealth setting is highly preferred but not required.

• Ideally strong understanding of intercompany transactions and basic corporate law (resolutions/filings) – this can be trained.

• Exceptional organizational skills with a "no task too small" attitude.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller 

Mississauga, ON - 5 days per week in office

$140,000–$150,000 base plus bonus and 407 assistance

Our client is an established organization within the real estate sector, known for its commitment to quality, community, and long-term growth. This is an exciting opportunity for an experienced Financial Controller to take ownership of the financial operations for a well-structured, large-scale business. The environment is collaborative, with leadership that supports initiative and continuous improvement.

Reporting directly to the CFO, the Financial Controller will oversee all financial management functions, including reporting, budgeting, compliance, and systems optimization. This position requires a professional with strong construction accounting experience.

Responsibilities

• Oversee all core accounting process including accounts payable, accounts receivable, payroll, and the general ledger.

• Ensure accurate transaction recording across development, construction, and home sales.

• Manage job costing, unit closings, and revenue recognition.

• Maintain effective internal controls and ensure data integrity throughout financial systems.

• Prepare timely and accurate monthly, quarterly, and annual financial statements.

• Collaborate closely with construction and operations teams to track budgets, costs, and project margins.

• Prepare and review lender draw requests, cash flow forecasts, and financial dashboards.

• Support annual budgeting, forecasting, and planning initiatives.

• Ensure full compliance with tax and accounting regulations.

• Oversee external audit processes and manage relationships with auditors.

• Complete all government filings, including HST/GST and corporate tax.

• Identify and implement process enhancements to improve accuracy and turnaround times.

• Lead and mentor accounting staff, providing coaching and career guidance.

• Foster a culture of accountability and professional growth.

Requirements:

• CPA designation.

• Significant experience within residential development or construction accounting.

• Strong understanding of job costing, WIP, and percentage-of-completion methods.

• Advanced Excel and financial modeling skills.

• Excellent analytical, communication, and leadership abilities.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller 

$130,000- $150,000 all in 

Mississauga, ON (in-office) 

My client is a family-owned real estate company in Mississauga, involved in all stages of property development—from land acquisition to construction and lease/sale. They are seeking a Controller to lead financial strategy, including cash management, budgeting, financial planning, and forecasting. This is an amazing opportunity for anyone in the construction space looking to grow their professional career.

Key Responsibilities:

• Build and maintain relationships with lenders

• Manage debt obligations and covenants

• Secure construction financing for projects

• Review and improve internal workflows

• Develop better KPIs, risk indicators, and reports

• Perform cost-benefit and investment return analyses

• Conduct financial risk assessments

• Analyze finances for projects and overall business strategy

• Oversee accounts receivable/payable, cash flow, and tax filings

• Manage payroll, regulatory compliance, and external audits

• Handle property insurance and tax issues

• Prepare financial statements (Balance Sheet, P&L, Cash Flow) and reports in line with GAAP

• Develop budgets, forecasts, and investment account reconciliations

Requirements

• Strong leadership and relationship-building skills

• CPA (CA, CMA, CGA) mandatory

• 5+ years at controller level or above

• Excellent communication, analytical, and problem-solving abilities

• Hands-on and adaptable, comfortable in a family business environment

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Accounts Payable Administrator (9-month contract position - potential for permanent)

Downtown, Toronto (4 days in office)

$55,000- $65,000 salary

Our client is a highly reputable property development and management company located in the heart of downtown Toronto (walking distance from Union). This role will report directly to the Manager, Accounting & Reporting and is an excellent opportunity to work in a fast paced, team environment. Please note that this role is a 9-month contract with potential to move to permanent, although it's not guaranteed. For this reason, we are giving preference to individuals who are not currently working and come from the real estate development industry. It is also worth noting that this role will include more than just Accounts Payable. It will also include accounting duties like bank reconciliations, HST filing, and more.

Responsibilities:

• Enter accurate and timely accounts payable invoices for each development project using established internal control practices.

• Process approved accounts payable invoices for payment.

• Maintain appropriate physical or electronic support for all accounts payable transactions.

• Create purchase orders in Excel for the development team and enter them into the Yardi system once approved.

• Input vendor invoices into the Yardi system weekly, ensuring correct legal entity and association with the appropriate contract, change order, or purchase order.

• Review vendor invoices for accuracy, including totals, taxes, billing entities, and matching them to purchase orders, contracts, and receiving reports.

• Verify vendor account status, respond to vendor inquiries, and ensure accounts are settled or outstanding balances are accurate.

• Follow up with vendors, development, and construction teams regarding monthly billing at month-end, ensuring all bills are received with correct supporting documentation.

• Assist with the development and implementation of new process improvement initiatives.

• Ensure all invoices entered are committed for payment in a timely manner and process cheques weekly.

• Ensure cheques have appropriate signatures.

• Determine the method of cheque delivery (mail, courier, or pick-up) in consultation with accountants.

• Ensure all bills are paid on time, and due dates are tracked appropriately.

• Update the vendor master list.

• Review the accounts payable aged listing monthly and follow up with accountants for any accounts payable over 30 days.

Requirements:

• 3-5 years of AP experience, preferably in real estate development

• Detail-oriented and organized

• Excellent communication skills

• Basic knowledge of Excel

If you would like to find out more about the role, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for an interview will be contacted.

If you are interested in learning more about this opportunity, please apply now by sending your resume to eric@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Vice President, Finance & Administration (Contract to Permanent)

$80 – $105 per hour 

Hybrid (Must be able to travel to Downtown Toronto office)

Our client, a specialized organization within the rights management sector, is recruiting for a Vice President of Finance & Administration. This is a contract-to-permanent opportunity, starting immediately on a temporary full-time basis.

Reporting to the Executive Director, this is a hands-on leadership role responsible for the full financial lifecycle - from royalty collection and investment tracking to complex distribution calculations and statutory reporting. This role is ideal for a detail-oriented financial leader who enjoys a mix of high-level oversight and operational accounting.

Key Responsibilities

• Royalty & Revenue Management: Oversee all duties relating to royalty collection and Accounts Receivable, ensuring accurate tracking of revenue streams.

• Complex Distributions: Calculate amounts for various distribution accounts (unallocated, disputed, contingency) for each royalty year, adjusting for interest, retransmitters, and audit outcomes.

• Investment Reporting: Manage investment activities, including entering trades into GP (Great Plains), reconciling statements, and creating monthly investment reports.

• Financial Reporting & Audit: Prepare monthly financial reports, update budget-to-actuals, and lead the annual financial audit process by providing detailed documentation on receivables and investments.

• Tax & Compliance: Manage all GST/HST monthly reporting, withholding tax reporting to the CRA, and the annual filing of T5 and NR4 forms.

• Operational Accounting: Oversee Accounts Payable, banking reconciliations, and the full payroll function.

About You

• 8–10+ years of experience in general accounting, reporting, and reconciliation.

• Strong understanding of Generally Accepted Accounting Principles (GAAP).

• Experience with the business practices of cable and satellite providers is highly preferred.

• Proficiency with Microsoft Dynamics GP (Great Plains) is an asset.

• Action-oriented with strong integrity and the ability to handle highly confidential information.

• Excellent communication skills, capable of building cooperative relationships with staff, collectives, and vendors.

If you are interested in this opportunity, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Director of Finance

Downtown Toronto (5 days per week in office)

$160,000 – $170,000 base + 20–25% bonus + excellent benefits

Our client is a leading investment firm with an extensive portfolio across different real estate asset classes. The firm is known for its long-term, disciplined investment philosophy and a culture that values collaboration, entrepreneurship, and excellence.

This is an outstanding opportunity for an experienced finance and accounting professional to join a highly reputable global platform.

As Director of Finance you will oversee all finance and operations for a major fund, driving financial reporting, liquidity management, compliance, and investor relations for a large, complex portfolio of real estate investments. Based in downtown Toronto, this role offers exceptional exposure to senior leadership and provides a meaningful pathway for professional growth within a high-performing organization.

Responsibilities

• Lead all fund-level finance and operations activities, including coordination with external administrators and oversight of quarterly financial and reporting

• Manage liquidity, treasury, and capital deployment functions to ensure efficiency and alignment with fund strategy

• Oversee compliance with investor, lender, and governance requirements, ensuring accurate and timely reporting

• Act as the subject matter expert for fund operations including valuations, performance measurement, and investor reporting

• Drive the preparation of audit materials, investor presentations, and performance analyses to support fundraising and due diligence efforts

• Collaborate with senior internal and external stakeholders to maintain strong financial controls and accurate entity-level reporting

• Mentor and develop finance team members, fostering growth and accountability within the group

• Lead continuous improvement initiatives to enhance reporting quality, efficiency, and transparency

Requirements

• CPA or CA designation required

• 7–10 years of progressive experience in accounting or finance, ideally within asset management, private equity, or real estate

• Must have IFRS (bonus points if you have worked with USGAAP)

• Demonstrated success managing teams and overseeing complex fund operations

• Advanced Excel and strong financial systems skills

• Excellent communication and stakeholder management skills, with proven ability to interact confidently at senior levels

• Highly organized, analytical, and detail-oriented with the ability to thrive in a fast-paced, evolving environment

This position offers a rare chance to join a globally respected organization at the forefront of real estate investing. You’ll work closely with exceptional leaders, gain exposure to diverse and impactful investments, and play a key role in advancing global decarbonization initiatives — all while being part of a collaborative and high-integrity team culture.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Accountant 

Toronto, ON – Onsite (5 days/week)

$100K-$125K base plus bonus and great benefits

Our client, a rapidly growing real estate investment and development firm, is seeking a Senior Accountant to take a lead role in accounting and financial reporting for multiple residential projects across the GTA. The company has a strong reputation for high-quality development, a collaborative culture, and a commitment to excellence in everything from acquisitions to construction and investor reporting.

This role offers an exciting opportunity to work closely with the CFO and senior leadership on financial operations, investor reporting, and project performance analysis while gaining exposure to the full development lifecycle. Within 6-9 months, this role will turn into a supervisory position.

Responsibilities

• Manage equity and debt draws for project ownership entities, partnerships, and joint ventures in coordination with cost consultants and lenders.

• Oversee monthly, quarterly, and year-end accounting for multiple projects, including HST returns, reconciliations, and reporting to external auditors.

• Support investor reporting, budgeting, and project performance tracking.

• Review and approve project invoices, ensuring compliance with contracts and budgets.

• Communicate with investment partners and internal executives on project financials.

• Identify and implement process improvements to streamline financial operations.

Requirements

• CPA designation (or in final stages).

• 3+ years of experience in external audit, preferably with exposure to construction or real estate clients.

• Strong technical accounting skills with advanced Excel proficiency.

• Excellent communication skills and ability to work collaboratively in a fast-paced environment.

If you are interested in learning more about this opportunity, please apply now by sending your resume to angie@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Vice President, Accounting & Finance – Real Estate

$200,000–$250,000 base plus 30% bonus and LTIP

4–5 days per week in the downtown Toronto office

Our client is an established, growth-oriented institutional real estate platform managing over $1.5 billion in assets. They are looking for a Vice President, Accounting & Finance to oversee all financial operations across their corporate, development, and fund structures. This is a key leadership role responsible for ensuring the company’s financial infrastructure, reporting, and governance meet the expectations of institutional investors and joint venture partners.

Responsibilities:

• Oversee all corporate and consolidated reporting in accordance with GAAP/IFRS.

• Lead financial operations across multiple entities, funds, and development projects.

• Manage audits, tax filings, and compliance with institutional-grade standards.

• Oversee development accounting, project finance, and construction draw processes.

• Support investor reporting, NAV calculations, and performance analyses.

• Lead system enhancements and automation initiatives (Yardi preferred).

• Provide strategic financial guidance to executive leadership and investors.

• Build and mentor a high-performing finance team.

Requirements:

• CPA designation required.

• 10–15 years of progressive accounting and finance experience within real estate, private equity, or investment management.

• Proven experience with institutional LPs, fund structures, or REIT environments.

• Strong knowledge of development and property accounting.

• Exceptional communication, leadership, and strategic insight.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller (initially a 9-month contract)

Downtown Toronto, ON - Hybrid

Compensation - $140,000-$160,000 (annualized), vacation, no benefits

We are seeking a hands-on, technically strong accounting professional for a critical 9-month engagement. The primary mandate is to own the integrity of their financial reporting, controls, and investor/lender reporting. This is a hands-on Director / Controller-level role reporting directly to the CFO, with real exposure across development entities, funds, valuations, financings, and tax. 

While this position may not convert to permanent, it offers high-level exposure to capital markets, debt management, financial accounting and planning, and operational restructuring. 

Responsibilities:

•  Full oversight of month-end, quarter-end, and year-end close

•  Consolidated financial reporting under ASPE & IFRS

•  Investor, lender, and bank reporting (including equity rolls & variances)

•  Cash flow forecasting, capital calls, loan drawdowns & distributions

•  Supporting financings and working closely with external auditors

•  Tax compliance (T2s, T5013s, HST, SLFI, CRA inquiries)

•  Leading analysts, strengthening controls, and improving finance processes

Requirements:

•  CPA designation required

•  5–7+ years of experience in real estate development or funds

•  Strong technical accounting and reporting background

•  Comfortable operating at both strategic and detailed levels

•  Collaborative, pragmatic, and able to thrive in a fast-paced environment

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller 

Downtown Toronto, ON - 4 days per week in-office

Compensation - $150,000-$160,000 (annualized), standard benefits and vacation

We are seeking a hands-on, technically strong accounting professional for a critical engagement. The primary mandate is to own the integrity of their financial reporting, controls, and investor/lender reporting. This is a hands-on Director / Controller-level role reporting directly to the CFO, with real exposure across development entities, funds, valuations, financings, and tax.

This position will offer high-level exposure to capital markets, debt management, financial accounting and planning, and operational restructuring. But, the team is very small, so you should expect to be very hands-on.

Responsibilities:

• Full oversight of month-end, quarter-end, and year-end close

• Consolidated financial reporting under ASPE & IFRS

• Investor, lender, and bank reporting (including equity rolls & variances)

• Cash flow forecasting, capital calls, loan drawdowns & distributions

• Supporting financings and working closely with external auditors

• Tax compliance (T2s, T5013s, HST, SLFI, CRA inquiries)

• Leading analysts, strengthening controls, and improving finance processes

Requirements:

• CPA designation required

• 5–7+ years of experience in real estate development or funds

• Strong technical accounting and reporting background

• Comfortable operating at both strategic and detailed levels

• Collaborative, pragmatic, and able to thrive in a fast-paced environment

If you are interested in learning more about this opportunity, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Manager, Finance (Real Estate Funds)(9-month contract with potential for permanent)

$140,000-$150,000 annualized salary

Downtown Toronto - Hybrid 

Our client, a real estate development group located in downtown Toronto, is recruiting for a collaborative and technical Senior Manager, Finance. This is an outstanding opportunity for a CPA with a background in real estate who enjoys fund-level financial management, investor reporting, and streamlining financial processes across a growing organization.

In this role, you will play a foundational part in monitoring fund performance, managing budgets, rolling forecasts, and operational plans. You will oversee the preparation of consolidated financial statements and manage the full cycle of fund reporting.

You will also play a major role in optimizing financial operations—assisting with cash activity (capital calls, distributions), managing lender reporting, and participating in process improvements including Yardi automation.

Key Responsibilities

• Oversee and coordinate the preparation of consolidated financial statements under both ASPE and IFRS.

• Prepare year-end working papers and work closely with external auditors to meet annual deadlines.

• Prepare quarterly financial statements and investor statements

• Prepare quarterly bank, lender, and investor reporting and compliance packages.

• Prepare tax working papers and review tax returns including T5013, T2, SLFI, and HST filings.

• Respond to various CRA audits and requests.

• Assist with cash activity such as capital calls, loan-drawdowns, distributions, and cash reconciliations.

• Monitor and project cashflows for funds on a short- and long-term basis.

• Review and assess external valuations and valuation inputs.

• Oversee and support Analysts regarding book maintenance and intercompany/chargeback billings.

About You

• CPA designation (CA or CMA preferred) is required.

• 5–7 years of relevant work experience within the real estate industry.

• Strong working knowledge of ASPE and IFRS principles within a real estate context.

• Experience with Yardi is mandatory.

• Ability to see the big picture while maintaining strong attention to detail.

• Excellent communication skills with the ability to explain technical concepts to non-finance stakeholders.

If you are interested in learning more about this opportunity, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Director of Special Loans

Toronto, ON – 4 days per week in the office

Competitive compensation with excellent benefits

We're seeking an experienced Director of Special Loans to join our client’s real estate finance team. This role is pivotal in handling distressed loans and minimizing risks within a real estate loan portfolio. You’ll be responsible for evaluating the financial health of borrowers, monitoring loan collateral, and working with internal teams, investors, and external partners to execute recovery strategies.

Responsibilities:

• Loan Restructuring & Workout: Lead the charge in restructuring troubled loans, developing tailored workout solutions, and negotiating terms with borrowers and stakeholders to optimize recovery.

• Loan Transaction Analysis: Dive deep into financials, market trends, and economic factors to assess loan performance and identify risks or opportunities.

• Portfolio Management: Support senior management in performing portfolio analysis, stress testing, and reporting on risks related to market conditions and loan concentrations.

• Stakeholder Collaboration: Work closely with internal finance, risk management teams, borrowers, investors, and external experts such as legal counsel, appraisers, and brokers.

• Compliance & Best Practices: Stay on top of industry regulations and ensure all strategies align with legal and regulatory standards.

• Team Development: Help train the team by identifying potential issues early in the lending process and conducting debriefs on loan workout outcomes.

Requirements:

• Proven experience with distressed loan management, ideally within the Canadian real estate sector.

• Strong financial analysis and risk assessment skills.

• Excellent negotiation and communication abilities.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Billing Specialist - (Accounts Receivable)

Downtown Toronto – Remote

$60,000–$65,000 base + discretionary bonus + excellent benefits

We are recruiting for a Billing Specialist to join a growing and dynamic organization in downtown Toronto. This is an exciting opportunity for someone who wants to take ownership of the billing cycle while also supporting finance, administration, and customer service functions. The role comes with a very flexible hybrid work setup, strong benefits, and tons of growth potential.

Responsibilities:

• Manage the full billing cycle—generating, reviewing, and sending accurate invoices on time.

• Reconcile payments, monitor receivables, and follow up on outstanding balances while maintaining strong client relationships.

• Ensure accuracy in revenue recognition and financial records.

• Support process improvements, automation, and efficiencies in billing and finance.

• Assist with reporting, reconciliations, and other ad hoc financial tasks.

• Provide administrative and customer service support, including responding to inquiries and assisting with onboarding.

• Coordinate events such as conferences, webinars, and team offsite.

Requirements:

• 3+ years of billing, bookkeeping, or AR experience (QuickBooks Online or similar).

• Strong organizational skills with attention to detail and accuracy.

• Excellent communication and customer service skills.

• Proactive, problem-solving mindset with the ability to streamline processes.

• Ability to handle a fast-paced environment and manage deadlines independently.

• Experience with billing automation tools or subscription-based billing is a plus.

If you are interested in learning more about this opportunity, please apply now by sending your resume to eric@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Property Accountant

Toronto, ON – Hybrid (4 days in-office)

$80,000–$90,000 base + bonus, RRSP plan, and excellent benefits

Our client is a leading commercial real estate company with a long-standing reputation for quality asset management and tenant service. Managing a well-maintained office portfolio across the GTA, they’re seeking a Senior Property Accountant to join their collaborative finance team.

This is a fantastic opportunity for an experienced property accountant who enjoys full-cycle accounting, detailed analysis, and working closely with property managers in a professional and supportive environment.

Key Responsibilities

• Manage full-cycle accounting for a commercial office portfolio, ensuring accurate and timely financial reporting.

• Prepare monthly financial statements, balance sheet reconciliations, and supporting schedules.

• Oversee CAM (Common Area Maintenance) and property tax reconciliations, including final billing adjustments.

• Assist with annual budgets, capital project reconciliations, and variance analysis.

• Prepare year-end working papers and liaise with auditors.

• Monitor cash flow, banking activity, and HST filings.

• Collaborate closely with property managers, responding to tenant and owner inquiries.

• Support process improvements and ensure strong internal controls are maintained.

What We’re Looking For

• 3–5+ years of commercial property accounting experience.

• Solid understanding of CAM and property tax recoveries.

• Proficiency in Yardi and advanced Excel skills.

• CPA designation or working toward completion.

• Excellent analytical, organizational, and communication skills.

• Ability to work independently and thrive in a fast-paced environment.

Why Join

• Stable and well-established company with long-term career growth potential.

• Strong team culture with approachable leadership.

• Comprehensive benefits package and RRSP matching.

• Exposure to a diverse commercial portfolio and cross-functional collaboration.

If you are interested in learning more about this opportunity, please apply now by sending your resume to angie@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Controller – Real Estate Investments

Location: North York (5 days per week in office)

Compensation: $140,000 – $160,000 base plus bonus

Excellent opportunity for a senior accounting professional to join an entrepreneurial real estate investment and management company based in North York. This is a hands-on, leadership role overseeing financial reporting, cash management, and the accounting team supporting a diverse real estate portfolio including multi-residential and commercial assets across Ontario. Priority will be given to individuals who have strong commercial property accounting experience.

Responsibilities:

• Oversee preparation and review of monthly, quarterly, and year-end financial statements and reporting packages

• Supervise general ledger, working papers, journal entries, and bank reconciliations to ensure accuracy and compliance

• Lead financial system enhancements and process improvements to drive efficiency

• Manage compliance with federal, provincial, and municipal reporting requirements including HST and corporate taxes

• Oversee budgeting, forecasting, cash flow, and financial analysis to support key management decisions

• Lead CAM and tax reconciliations, capital calls, and investor distributions

• Coordinate year-end audit and liaise with external auditors

• Mentor and develop a high-performing accounting team

Requirements:

• CPA designation (CA, CMA, or CGA) strongly preferred

• Minimum 10 years of progressive accounting experience, ideally in commercial real estate

• Strong technical accounting background with a focus on reporting accuracy and timeliness

• Experience with Yardi or similar real estate accounting software

• Proven leadership skills and the ability to thrive in a fast-paced, growth-oriented environment

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Vice President Capital Markets - Capital Raising (Retail)

Victoria, British Columbia (hybrid in office)

Competitive compensation made up of base plus bonus

Our client is a growth-oriented, BC-based real estate investment firm primarily focused on multi-residential development and management across the country.

The VP of Capital Markets is a newly created role and will be an important role in the Company’s platform growth including fund raising, corporate development and product development. This is a broad role with significant responsibility, well suited to an individual with significant fund raising and client management experience, now looking to apply it in a hands-on, entrepreneurial and platform building environment. The company is seeking an individual who can leverage their pre-existing private, retail, and potentially institutional client relationships to lead the capital raising initiatives.

With established expertise in capital raising and investment structuring, the incoming VP of Capital Markets will be an instrumental figure in establishing fundraising channels for the various investment mandates being undertaken by our client. The key area that you will be focused on will be Retail. The company has a great track record with an existing investor pool, but will like this person to join and help grow the investor base. 

Roles & Responsibilities

• Build and maintain strong relationships with prospective and current investors, with a focus on HNW and Family Office segments.

• Maintain technical knowledge of the company’s offerings to provide the best solutions for investors.

• Clearly communicate the offerings and assist investors with due diligence questions and investor subscription process, where appropriate from a legal and regulatory perspective.

• Use CRM software to track business development efforts and progress achieved.

• Assist in marketing efforts such as creating investor presentations, webinars, and educational materials.

• Assist in structuring and successfully launching new investment mandates for the investors.

• Establish, maintain, and engage with industry relationships including advisors, lenders, brokers, legal counsel, and accountants.

Qualifications & Experience

• 7+ years of investment sales experience, with a proven track record in developing and growing Assets Under Management.

• Located in BC to be able to work onsite at times.

• Intimate understanding of financial products that serve the interests of institutional and high-net-worth investors.

• Experience in raising capital from family offices, UHNW individuals and HNW families or institutional avenues.

• A self-starter who can manage individual responsibilities and maintain overall awareness of management priorities.

• Excellent communication skills and ability to work in a team setting.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Accountant

Mississauga, ON (Oakville/Mississauga Area) 

$80,000 - $90,000, plus bonus, full benefits, and vacation

Our client is a stable, growing business known for its established presence and positive, tenured work environment. They are seeking a proactive Senior Accountant to join their team of professionals. This role encompasses a broad range of accounting and analysis duties, including full-cycle accounting, project analysis, and crucial reporting functions, with mentorship from corporate accounting leadership.

Responsibilities:

• Perform full-cycle accounting duties for various corporate and investment entities, including Accounts Payable (AP), Accounts Receivable (AR), and intercompany transactions.

• Complete and reconcile bank statements on a monthly basis.

• Prepare comprehensive monthly project reports for distribution to internal management and external investors.

• Maintain accounting records for managed entities and ensure supporting information for all financial transactions is complete and accurate.

• Assist the Corporate Controller with cash management tasks, including the preparation of monthly cash draws.

• Prepare monthly investor reporting templates and submit monthly indirect tax returns (e.g., HST).

• Facilitate the preparation of annual corporate tax returns by coordinating with external auditors.

• Assist with tax and financial audits as required.

• Maintain the company’s internal document management system.

• Provide weekly sales reporting and ad-hoc financial analysis as needed.

• Perform any other finance and accounting tasks as assigned by the Corporate Controller.

Key Requirements:

• University Degree with an Accounting focus or a College Accounting Diploma.

• 3-4+ years of experience in a progressive general accounting position.

• Excellent organizational skills coupled with a "can-do" attitude.

• Great communication skills (both oral and written).

• Familiarity with accounting software.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Property Accountant

Toronto, Ontario - hybrid downtown

$90,000-$100,000 base plus bonus, group retirement plan, and great benefits

Our client is an organization where you join, grow, and stay for a while. People are tenured and they typically promote from within as they continue to grow. If you’re in property accounting and live in Toronto, this is the role for you!

The team is looking for a senior property accountant who is coming with experience doing residential property accounting. They will offer you the opportunity to learn commercial property accounting as well. You do not need to come with that specific experience.

This company has a great reputation and is growing so it’s a great time to join. The reason for the opening is because of growth of the portfolio.

Responsibilities:

• Responsible for the full cycle day-to-day accounting which includes: recording transactions, accruals, reviewing accounts payable, completion of bank reconciliations, HST returns, and reconciliations of inter-company transactions and balance sheet accounts.

• Prepare CAM and Tax recoveries and reconciliations for properties.

• Prepare monthly cash flow projections and cash distributions.

• Review and generate monthly billings for tenants.

• Liaise with property management, leasing and other departments pertaining to daily operations.

• Oversee lease setup and create recovery models for newly acquired properties.

• Month-end close procedures, including the preparation of monthly financial statements and financial reports, as well as monthly variance analysis and discussion to support budget overages and margin erosions for assigned properties.

• Work with property management and other parties to prepare annual budgets and reforecasts.

• Assist with year-end audit processes and quarterly reviews through the preparation of audit working papers.

• Identify opportunities for process improvements or efficiencies.

• Other ad-hoc projects.

Responsibilities:

• College diploma or University degree

• Minimum of 2-3 years of experience in Property Accounting

• Excellent verbal and written communication skills

• Advanced MS EXCEL skills and proficient with MS Word and Outlook

• Experience with the integration of all accounting related activities on property acquisitions

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Accountant

Toronto, ON (On-site)

$85,000-$95,000 base plus 10% bonus and excellent benefits and stock options

Our client is a reputable company in the services industry. They are seeking a Senior Accountant to work on finance and accounting duties, including the month-end close, the coordination of the year-end audit process, the development of new financial reports, budgeting and forecasting, while ensuring constant adherence to internal financial controls and up to date with accounting standards. We are looking for an entrepreneurial CPA-designated senior accountant who has a solid background in reporting and wants to join a growing PE-backed tech company.

Responsibilities:

• Financial Planning & Analysis: Lead the preparation of financial models, budgets, and forecasts, analyzing key drivers, trends, and variances.

• Performance Metrics: Develop and track key performance indicators (KPIs) for various service lines, including patient volume, treatment success rates, and cost efficiencies.

• Strategic Support: Provide financial insights for business development opportunities, capital investments, and new service offerings, supporting leadership in making informed decisions

• Transactional Accounting: Provide support to the entire accounting team when someone is away – AP, AR, payroll, etc.

• Cost Analysis: Perform detailed cost analysis of clinical operations and patient treatments, identifying opportunities for cost optimization without compromising quality of care.

• Revenue Cycle Management: Monitor revenue cycle processes to ensure timely billing and collections, and provide analysis on payer mix, reimbursement rates, and patient payment trends.

• Variance Analysis: Conduct in-depth analysis of monthly, quarterly, and annual financial performance compared to budget, providing insights on deviations and recommending corrective actions.

• Regulatory Compliance: Ensure financial compliance with healthcare industry regulations and reporting requirements.

• Ad-hoc Analysis: Support senior management with ad-hoc financial analysis and reporting as needed.

Qualifications:

• Bachelor’s degree in Accounting/Finance preferred

• CPA designated

• 5+ years of financial experience

• Strong process improvement skills as well as profitability analysis knowledge

• Excellent analytical (advanced MS Excel skills) and strong communication skills

If you are interested in learning more about this opportunity, please apply now. Due to the high volume of applicants, only those selected for an interview will be contacted.

If you are interested in learning more about this opportunity, please apply now by sending your resume to angie@winchesters.ca
Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Finance Manager

Downtown Toronto, ON – 4-5 days per week in office

$90,000–$110,000 base + stock options, excellent benefits, and strong growth potential

Our client is an innovative, fast-scaling software company with a strong North American presence and significant U.S. market traction. Their focus is on delivering tech-driven solutions backed by exceptional customer service, helping clients modernize and optimize their operations.

They are looking for a Financial Manager to take full ownership of the accounting function. This is a hands-on role where you’ll oversee day-to-day accounting, multi-entity reporting, compliance, and financial operations while working closely with the CEO and external partners. It’s an opportunity to make a direct impact by tightening processes, driving efficiencies, and setting up the finance team for the next stage of growth. The client does require an individual to have worked in an external audit firm before.

Responsibilities

• Manage full-cycle accounting across three entities, ensuring accuracy and timeliness

• File HST returns and ensure compliance with tax requirements

• Handle multi-currency transactions and reconciliations

• Partner with external accountants on audits and year-end reporting

• Oversee payroll processing to ensure accuracy and timeliness

• Lead AP/AR, bank reconciliations, and expense management

• Introduce process improvements and strengthen internal controls

• Deliver clear financial reporting, budgeting, and analysis to support leadership

• Act as a trusted advisor to management on performance and growth initiatives

Requirements

• CPA designation

• 4+ years of progressive experience in accounting/finance

• Hands-on work style - you will be the only accountant in this company until they grow more

• Experience having worked at an external audit firm

• Strong organizational skills, self-starter attitude, and proactive mindset

• Ability to thrive in a dynamic, high-growth environment

Why This Role Stands Out

• Stock options with exciting upside – company is preparing for a Series A 

• Excellent benefits package (including dental and vision)

• 3 weeks’ vacation to start

• Clear career progression as the company scales

• Entrepreneurial culture that values initiative, ownership, and results

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Accountant

Mississauga, ON – Onsite (4–5 days/week)

$85,000 – $95,000 base plus bonus

Our client is a very stable investment company based in Mississauga, Ontario. They are known for their supportive and positive culture, reasonable hours, and being an overall lovely place to work. While the role itself offers limited long-term growth, it provides stability, great work-life balance, and the chance to be part of a genuinely welcoming environment.

This Senior Accountant position will be responsible for full-cycle accounting across multiple entities, including management companies, project entities, and investor entities. The successful candidate will manage monthly accounting processes, financial reporting, and project accounting, as well as assist with year-end financials and external audits.

Responsibilities

• Maintain monthly accounting records, including AP, AR, bank reconciliations, and intercompany transactions

• Prepare and file HST returns

• Assist with cash management and planning

• Facilitate preparation of annual corporate tax returns with external auditors

• Support year-end financial statement preparation (experience required)

• Contribute to investor reporting and project accounting

• Assist with tax and financial audits

• Maintain complete and accurate supporting documentation

Requirements

• 5–8 years of relevant accounting experience

• Strong EXCEL and Microsoft Office proficiency

• Excellent organizational and communication skills

• Self-motivated, able to work under deadlines

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Analyst Commercial Mortgages

Downtown Toronto | 3 Days In-Office

$85,000–$100,000 Base + Bonus + Excellent Benefits

We’re recruiting for a Senior Commercial Mortgage Analyst on behalf of a growing real estate finance firm in downtown Toronto. This role is ideal for a detail-oriented professional with experience in commercial mortgage operations, particularly around renewals and underwriting. You’ll be part of a collaborative team with strong support, excellent benefits, and great work-life balance.

Responsibilities:

• Manage a portfolio of commercial mortgage renewals, assumptions, and investor sales

• Review underwriting binders, commitment letters, and supporting documents for completeness and accuracy

• Liaise with lawyers, insurers, investors, and internal stakeholders to ensure all conditions are met

• Accurately update and maintain loan details in internal systems

• Maintain and update various internal reports used by senior management and investors

• Provide support and training to junior team members

• Review and approve transactions processed by other analysts

• Perform quality control on files prior to securitization

• Assist with AML compliance reviews and documentation

• Review financial transactions including EFTs, deposits, and cheque requisitions

• Take on special projects and provide backup support as needed

Requirements:

• 4+ years of experience in the mortgage or financial services industry

• Strong understanding of mortgage renewals, assumptions, and commercial loan documentation

• High level of accuracy and attention to detail

• Proficiency in Microsoft Excel and Word

Why Apply:

• Excellent compensation and benefits package

• Great work-life balance (only 3 days/week in-office)

• Stable, supportive team with growth potential

• Bright, modern office with ongoing training and social events

If you are interested in learning more about this opportunity, please apply now by sending your resume to eric@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller

Downtown Toronto, ON (hybrid)

$120,000-$130,000 base plus discretionary bonus, full health and dental benefits 

Our professional services clientis a leading Canadian organization based in downtown Toronto with a reputation that is worldwide. The firm is recognized for excellence across a broad range of building types. The company is a leading proponent of sustainable design innovation and is continuously one of Canada’s top employers.

We are seeking an enthusiastic experienced to join their Accounting and Finance team as the new Financial Controller. This is an excellent role that will involve the candidate in various aspects of the finance related activities. The ideal candidate will have great GL accounting and financial statement prep experience, excellent verbal and written communication skills, very good organizational skills, and be able to multi-task in a busy office. This is a full-time position. Working hours are from Monday to Friday, 9:00 a.m. – 6:00 p.m. with summer hours and holiday closure.

Key responsibilities:

• Full financial responsibility for month-end, quarter-end and year-end financial reporting

• Preparation of monthly financial reporting package for Canada and the US

• Financial planning including annual budgeting, forecasting and variance analysis

• Tax and statutory Compliance and Filings

• Revenue recognition for all active projects

• Oversee and develop best practices for AP, AR and GL functions

• Manage and mentor accounting staff

• Annual audit

• Process improvement and establish adequate internal controls

Required background:

• A degree

• CPA designation

• Minimum seven years of professional accounting experience required

• Advance EXCEL and computer skills

• Some experience in working with multi-currency, multi-entity organizations

• Ability to excel in a team environment and have the confidence to manage people effectively

• Excellent communication and interpersonal skills

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller

Downtown Toronto – Onsite (4 days/week)

$130,000 – $140,000 base plus discretionary bonus

Our client is a highly regarded organization that has consistently been recognized as one of Canada’s top employers. They offer an excellent workplace culture, competitive compensation, and a strong focus on employee well-being.

This Financial Controller position will play a key role in overseeing financial management, payroll, reporting, and compliance across the organization. The successful candidate should bring strong technical accounting skills, leadership experience, and the ability to manage both routine processes and year-end audit work with external auditors.

Key Responsibilities

• Oversee full-cycle accounting and financial reporting across multiple entities

• Manage general ledger, month-end, and year-end closing processes

• Ensure accuracy and timeliness of monthly, quarterly, and annual reporting

• Supervise and mentor accounting staff, including payroll, GL, and AP

• Oversee payroll functions and ensure compliance with regulations

• Coordinate and manage year-end financial statement preparation with external auditors

• Lead budgeting, forecasting, and variance analysis processes

• Ensure compliance with accounting standards, tax regulations, and internal controls

• Identify and implement process improvements to enhance efficiency

Qualifications

• CPA designation required

• Bachelor’s degree in Accounting, Finance, or related field

• 7+ years of progressive accounting/finance experience, including at least 3 years in a leadership role

• Experience overseeing payroll and year-end audit processes is essential

• Experience in multi-entity, multi-currency organizations is an asset

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Project Accountant

Toronto, ON - on the transit line

$90,000 - $100,000,000 compensation, 5 weeks of vacation, strong benefits

The company is a real estate private equity firm looking to hire a senior project accountant to handle true full-cycle project accounting for a number of projects. There are a ton of growth opportunities in this business.

The role of the Senior Project Accountant will be managing the costs, budgets, and accounting for several projects. You will report to a CPA-designated VP in this small group. The office attire is business professional. Bonus points if you like to get involved in company outings, etc.

Responsibilities

• Review payables for accuracy

• Assess any escalated payable matters and discuss resolutions with Project Management team

• Provide, maintain, and record any issues/concerns about payables

• Ensure timely and accurate billings by working with PM team to ensure all deadlines are met, and all billings are reflective of percentage of completion

• Work closely with clients to ensure demands are met, ensuring valid documentation and variance analysis

• Ensure variances are accounted for

• Ensure change orders are billed correctly and in full, in a timely manner

• Prepare monthly project summary of the cost and revenue details with analysis

• Analyze monthly payroll and post journals

• Prepare monthly bank reconciliations and report to the Director on cash

• Assist with ad hoc projects as required, including year-end working paper preparation, and assist with annual external review by responding to auditor inquiries

• Assist with monthly forecast preparation

Requirements

• Diploma or university degree

• 2-3 years of project accounting experience minimum

• Strong organizational skills with an ability to prioritize tasks with a keen attention to detail

• Strong communication skills – written and oral

• Priority will be given to individuals coming from construction or development but it is not required

• Proficient in data entry and document management

If you are interested in learning more about this opportunity, please apply now by sending your resume to eric@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Director of Commercial Real Estate Underwriting

Toronto, ON - hybrid

$150,000-$175,000 plus 25% bonus and excellent benefits

Are you a driven, detail-oriented professional with a passion for commercial mortgage underwriting? We’re on the hunt for a dynamic Director of Commercial Underwriting to join a fast-paced and entrepreneurial team and supervise three underwriters. If you’re ready to lead and thrive in a high-energy environment, this role could be your perfect match.

What You’ll Be Doing:

• Managing and developing the Underwriting & Portfolio Management team, including training new hires.

• Overseeing the underwriting and funding process.

• Managing resource allocation and prioritizing deals.

• Ensuring the timely submission of loan applications and funding documents to institutional and private investors.

• Performing quality control on all loan applications and fundings (you’ll be the second signature).

• Conducting thorough risk assessments and ensuring consistency.

• Acting as a key contact for investors, addressing questions, and ensuring timely loan adjudication and funding.

• Building and maintaining relationships with institutional and private investors.

• Staying up to date with industry knowledge, competition, and market trends.

• Collaborating closely with support staff and the executive team.

What You’ll Bring to the Table:

• A post-secondary degree in Commerce, Business Administration, Economics, or Finance, with a focus on Real Estate or Land Development.

• 5+ years of related experience in the real estate lending industry.

• Management and supervision experience required.

• Exceptional communication skills, both written and verbal, with acute attention to detail.

• Proven leadership, organizational, and time management skills.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Accountant 

Toronto, ON – Onsite (5 days/week)

$85K-$110K base

Our client, a rapidly growing real estate investment and development firm, is seeking a Senior Accountant to take a lead role in accounting and financial reporting for multiple residential projects across the GTA. The company has a strong reputation for high-quality development, a collaborative culture, and a commitment to excellence in everything from acquisitions to construction and investor reporting.

This role offers an exciting opportunity to work closely with the Controller and senior leadership on financial operations, investor reporting, and project performance analysis while gaining exposure to the full development lifecycle.

Responsibilities

• Manage equity and debt draws for project ownership entities, partnerships, and joint ventures in coordination with cost consultants and lenders.

• Oversee monthly, quarterly, and year-end accounting for multiple projects, including HST returns, reconciliations, and reporting to external auditors.

• Support investor reporting, budgeting, and project performance tracking.

• Review and approve project invoices, ensuring compliance with contracts and budgets.

• Communicate with investment partners and internal executives on project financials.

• Identify and implement process improvements to streamline financial operations.

Requirements

• CPA designation (or in final stages).

• 3+ years of experience in external audit, preferably with exposure to construction or real estate clients.

• Strong technical accounting skills with advanced Excel proficiency.

• Excellent communication skills and ability to work collaboratively in a fast-paced environment.

If you are interested in learning more about this opportunity, please apply now. Due to the volume of applicants, only those selected for interviews will be contacted.

Controller – Part-Time Ongoing Contract 

$50–$60 per hour 

2–3 days per week in-office, Bowmanville

Our client, a well-established group, is recruiting for a part-time Controller to support their operations on an ongoing contract basis. This role offers a flexible schedule with 2–3 days per week in the Bowmanville office and will be responsible for overseeing the full accounting function in a hands-on capacity.

Responsibilities:

• Oversee Accounts Payable, including reviewing all invoices for active projects, operations, and overhead, coding to proper cost codes, and ensuring appropriate cheque processing.

• Manage cash flow, including daily bank reconciliations, maintaining detailed cash sheets, and preparing weekly reports to ownership.

• Take ownership of project billings, including compilation, submission, and timely collections.

• Oversee payroll approval and compliance with government remittances (HST, WSIB, source deductions, T4s, T5018s).

• Prepare monthly internal financial reports, including income statements, balance sheets, and individualized project reporting.

• Coordinate with external accountants for year-end working papers, address audit inquiries, and ensure quarterly/annual reporting requirements for lenders and bonding companies are met.

Requirements:

• Solid accounting experience within the construction sector.

• Strong knowledge of project accounting and cash management.

• Ability to work independently and manage multiple priorities.

• Hands-on approach with excellent attention to detail.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller – Real Estate

$140,000 – $160,000 base plus bonus

North York, ON - In-office

This is an excellent opportunity to join a growing and entrepreneurial real estate investment company with a strong and diverse portfolio. As Financial Controller, you will play a key role in leading the accounting function, managing a team, and supporting senior management with financial insight to drive strategic decisions. This role reports into a CFO and offers a mix of review of property accounting, leadership, and process improvement, making it ideal for someone looking to step into a high-impact position. At times, hours will be a bit longer.

Responsibilities:

• Prepare and review monthly, quarterly, and year-end financial statements and reporting packages

• Oversee general ledger, journal entries, and bank reconciliations to ensure accuracy

• Lead and mentor a small accounting team

• Review monthly accounting packages 

• Drive improvements in financial systems, templates, and reporting efficiency

• Ensure compliance with regulatory filings and remittances

• Provide financial analysis to support asset management decisions

• Manage daily cash flow and banking relationships

• Assist with annual budgets, forecasts, and business plans

• Take on additional projects and responsibilities as needed

Requirements:

• Accounting designation (CPA) preferred

• 5+ years of progressive experience in property accounting

• Supervisory or team leadership experience

• Strong knowledge of real estate accounting and reporting systems (Yardi an asset)

• Detail-oriented with a focus on accuracy and timeliness

• Strong communication and presentation skills

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Assistant Financial Controller

Downtown Toronto, ON (3 days per week in the office)

$125,000 – $135,000 + bonus & benefits

Our client is a public company with an excellent reputation. They pride themselves on work/life balance which is also reflected in their hybrid work model. The team is looking to fill a newly created role - Assistant Financial Controller to oversee full-cycle corporate accounting, internal controls, transactional accounting, cash management, general ledger maintenance, fixed assets, and more. This role reports to the VP Finance and plays a key part in budgeting, intercompany accounting, and monthly close processes. While it is not required, they would love to find a person coming with multi-currently experience. Applicants should have worked at a public company at some point in their career.

Key Responsibilities:

• Manage full-cycle accounting and month-end close

• Oversee general ledger, journal entries, and reconciliations

• Prepare budgets, forecasts, and internal financial reports

• Support treasury and debt management activities

• Assist with financial statements and tax filings

• Maintain intercompany accounts and support fund flows

• Identify process improvements and assist with system implementations

• Contribute to internal control development and documentation

Qualifications:

• CPA designation

• 5+ years of accounting experience, preferably in a multinational setting

• Strong IFRS knowledge is an asset

• Proficient in Excel

• Strong communication skills

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller

Mississauga, Ontario

$110,000-$130,000 base plus bonus and great benefits

Our client is a stable and growing real estate company in Mississauga, looking for a Financial Controller.

Our stable and experienced client is located in Mississauga and is looking for a financial controller to join the business who has more than just strong accounting experience. The business has been going through an exciting transformation as they streamline processes, go more paperless and improve/automate processes across the accounting department. The Financial Controller will manage the accounting and control functions, reporting the results of operations, while implementing these new changes across the department. The Controller will also be responsible for annual financial statements and tax returns for 100+ legal entities, investor reporting, cost controls, financial and cash planning along with financial/tax audits.

Responsibilities:

• Lead all day-to-day accounting operations and supervise staff members, including updating accounting records, monitoring bank accounts, completing monthly reconciliations, AP, AR, Payroll, General Ledger, Cost Ledger, etc.

• Assist with projects’ financing and prepare application package.

• Prepare the annual corporate budget in consultation with the CFO.

• Recommend and prepare documentation for distributions and investment of excess funds.

• Maintain company bank accounts ensuring all transactions are appropriate.

• Create and maintain cash flow forecast to ensure financing needs are met.

• Establish financial statement reporting timelines and supervise implementation.

• Implement and maintain a robust internal control system.

• Prepare monthly, quarterly and annual financial reporting package in accordance with ASPE.

• Assemble information for and liaise with external auditors.

• Oversee preparation and review of all tax filings and returns to ensure compliance with tax legislation, HST, CPP, EI, EHT, WSIB, T2, T5013, etc.

• Document and maintain complete and accurate supporting information for all financial transactions.

• Develop and maintain financial accounting systems for cash management, accounts payable, accounts receivable, credit control, and petty cash.

• Reconcile bank accounts. Review monthly results and prepare monthly variance reporting. Manage the cash flow and prepare cash flow forecasts.

• Prepare board materials including summarizing financial information, trend and variance analysis and summarize key performance indicators.

• Oversee and review interim and final closing and cash distribution to JV partners and investors.

• Develop and manage an effective costing system for the projects.

• Prepare Tarion related application and reports: vendor/builder registration, units’ enrollments, annual renewal, etc.

Requirements:

• Degree or diploma and CPA designation completed

• A minimum of 5 years of relevant experience

• Supervisory experience over at least 3 individuals

• Real estate and construction industry experience would be an asset but is not mandatory

• Strong background with internal controls

• Proficiency in MS Office, including Word, Excel and Outlook

• Ability to communicate effectively, both verbally and in writing

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Manager, Finance and Accounting

North York – In office 5 days per week

$110,000–$125,000 base salary

Full-time – 12 to 18 month contract

We’re recruiting for a Finance & Accounting Manager to join a growing real estate investment company in North York. This is a demanding and fast-paced role that requires someone with strong technical skills, leadership ability, and a sharp eye for process improvements. You’ll be managing a small accounting team and working closely with leadership on reporting, audits, budgets, and financial analysis. This role is fully on-site and will require longer hours at times, so it’s best suited to someone who enjoys rolling up their sleeves and taking ownership of complex accounting work.

What you’ll be doing:

• Managing and reviewing monthly financial packages from third-party property managers

• Preparing quarterly reporting for a portfolio of multi-residential assets

• Reviewing monthly variance analysis on commercial and residential properties

• Supporting the annual budget process and preparing CAM/tax reconciliations

• Overseeing year-end working papers and liaising with auditors

• Leading and mentoring a small accounting team

• Improving accounting templates, reporting processes, and financial systems

• Supporting the Controller with special projects and system upgrades

What we’re looking for:

• 5+ years of progressive accounting experience

• Experience in real estate (multi-residential and/or commercial) preferred

• CPA or CPA-eligible strongly preferred

• Proficiency in Excel; Yardi experience is a bonus

• A proactive mindset and strong attention to detail

• Able to work independently in a fast-paced, high-expectation environment

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Financial Accountant – Real Estate Investment

Downtown Toronto, Ontario - onsite

$90,000–$105,000 base plus 10% bonus, 4 weeks of vacation, and excellent benefits

Our client is a leader in real estate investment with a diverse portfolio spanning across North America. This is an exciting opportunity to join a high-performing corporate finance team at a company known for innovation, professionalism, and long-term growth.

Winchesters is proud to be partnering with them again as they continue to build their Toronto-based finance and accounting function. This Senior Financial Accountant position is ideal for a CPA coming out of public accounting (Big 4 or mid-tier), or someone already in industry looking for broader exposure in real estate, investment reporting, and cross-functional finance initiatives.

The successful candidate will report to the Director of Finance and collaborate with asset managers, capital markets teams, and an offshore finance group. The role touches on financial reporting, forecasting, audits, intercompany reconciliations, and fund analytics — with high visibility and opportunity for progression.

Key Responsibilities:

• Review monthly and quarterly financial reporting packages from operating partners to ensure completeness and accuracy

• Oversee the onboarding/offboarding of investments, including due diligence on structures, funding, and reporting setup

• Support intercompany reconciliations and simplify reporting processes across entities

• Prepare IFRS-compliant reporting deliverables, co-investor statements, and performance packages

• Partner with capital markets on financing/refinancing activities

• Assist in quarterly reforecasts and long-range planning across income statements and cash flow models

• Support cross-functional ad hoc initiatives and contribute to broader FP&A deliverables

Requirements:

• CPA designation (CPA, CA preferred)

• 2-3+ years of experience in public accounting or a combination of audit and industry

• Strong technical knowledge of IFRS and financial consolidations

• Experience working with real estate, investment, or asset management companies is an asset

• Proficiency with Microsoft Excel (pivot tables, VLOOKUPs, modelling) and PowerPoint

This is a unique opportunity to join a world-class real estate investment group in a role that offers both technical depth and strategic exposure. If you’re looking for a finance position with long-term growth and meaningful responsibility, we’d love to hear from you.

To apply, please send your resume in confidence to angie@winchesters.ca or visit www.winchesters.ca.

Please note: Due to a high volume of applicants, only those selected for an interview will be contacted.

Senior Manager, Corporate Accounting

Toronto, ON (hybrid)

$140,000–$180,000 base plus bonus and excellent benefits

Our client, a leading real estate firm, is seeking a Senior Manager of Corporate Accounting to join their growing finance team. This is a high-impact role with a clear path to Controller within two years. The successful candidate will lead corporate financial reporting, oversee tax and accounting operations, and manage a small team.

Key Responsibilities:

• Lead the monthly close and tax reporting cycle across multiple corporate entities

• Oversee budgeting, forecasting, and variance analysis

• Manage two direct reports

• Maintain strong internal controls and improve financial processes

• Manage cash flow, payroll, and intercompany transactions

• Act as the primary liaison with external accountants for tax compliance and year-end filings

• Support senior leadership with ad hoc reporting and financial analysis

• Monitor changes in tax legislation and assess implications for the business

• Prepare and review corporate tax filings (T2s, T5s, T5013s)

Requirements:

• CPA designation required

• Minimum of 6 years of progressive accounting experience, including 2+ years in a leadership role

• Strong technical accounting and tax knowledge

• Experience in real estate or development is an asset but not required

• Advanced Excel skills and proficiency with financial systems

• Strong communication, organizational, and analytical skills

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Corporate Accountant
Downtown Toronto (Hybrid)
$85,000–$95,000 base plus bonus

We are recruiting for a Senior Corporate Accountant on behalf of a growing and well-established investment management company. This is a great opportunity for a CPA with strong full-cycle accounting experience to join a collaborative and high-performing finance team.

Key Responsibilities:

• Oversee day-to-day corporate accounting, including journal entries, general ledger, cash, payables, and fixed assets

• Reconcile intercompany transactions, including cash transfers and management fees

• Perform monthly bank reconciliations and foreign currency revaluations

• Prepare working papers and month-end journal entries (accruals, prepaids, amortization, etc.)

• Analyze variances and provide commentary

• Prepare HST returns and support budgeting processes

• Assist with audit preparation and support

• Contribute to process improvements and special projects

What We’re Looking For:

• CPA designation

• Minimum 3 years of corporate accounting experience

• IFRS knowledge and experience in a multi-currency environment

• Strong Excel skills (Yardi is an asset)

• Detail-oriented, analytical, and able to manage deadlines

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller

$130,000 – $145,000 base plus bonus and excellent benefits

4-5 days per week in the Mississauga office

Our client is recruiting for a Financial Controller to join their growing team. This business has been experiencing steady growth and offers strong potential for career advancement. Due to growth, this is a newly created position to oversee a small accounting team.

As Financial Controller, you will oversee all accounting, financial reporting, and internal control activities. You will lead a small finance team, manage relationships with auditors and tax advisors, and support the CFO with budgeting, forecasting, and cash flow management. This is a hands-on role where you will be a key business partner, driving operational efficiency and supporting decision-making with insightful financial analysis.

Key Responsibilities:

• Oversee all accounting operations, including AP, AR, payroll, job costing, WIP accruals, and the general ledger

• Manage month-end and year-end close processes and prepare accurate financial statements

• Lead budgeting and forecasting, analyzing results and providing recommendations to management

• Manage cash flow, banking relationships, and treasury functions

• Ensure compliance with all internal controls, regulatory, tax, and payroll requirements

• Coordinate audits and tax filings with external advisors

• Implement and optimize financial systems, reporting tools, and processes

• Partner with operations and project management teams for accurate job costing and profitability analysis

• Mentor and develop the finance team, fostering accountability and continuous improvement

Qualifications:

• CPA designation required

• 6-8 years of progressive accounting experience, including at least 2-3 years in a leadership or Controller role

• Preference for candidates with construction industry and external audit firm backgrounds

• Strong technical knowledge of ASPE, financial reporting, and internal controls

• Experience with job costing, WIP accruals, and ERP systems

This is an excellent opportunity for an ambitious finance professional to join a growing business and have a significant impact.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Associate - Real Estate Development Investments

Downtown Toronto, ON - hybrid

$100,000-$125,000 base plus bonus and benefits

Our client is a well-established real estate development firm looking to hire a Senior Associate of Development Investments. This is an excellent role for a an real estate professional who has a strong financial modelling skillset and has participated in underwriting new investment opportunities to acquire land and development residential assets. Bonus points if you have experience modelling purpose-built rental projects. The client would like an individual who has experience with development projects from acquisition to completion of the development or disposition, taking a proactive role to manage risk and maximize returns. As this is a smaller entrepreneurial development firm, you will be able to gain experience in so many different areas of the business. Ideally you will stay and grow with the company to eventually hire junior staff in the future.

Responsibilities:

• Participate in underwriting new investment opportunities to acquire land and develop residential assets

• Create the pro forma, assist the VP in coordinating all underwriting and acquisition activities, prepare the Investment Committee memo, present to the Investment Committee and prepare all necessary investor presentations, investment offering documents and legal agreements

• Oversee the execution of development plans for active development projects from acquisition to completion of the development or disposition taking a proactive and “hands-on” approach to managing risk and maximizing returns on all projects

• Participate in all key project decisions and critical project management meetings through the entire development life cycle (planning, design, sales, permits, construction and delivery phases) to ensure the project is delivering on time and on budget.

• Review, critically assess and prepare project cash flows and pro forma financial projections

• Regularly evaluate market conditions to identify changes that give rise to opportunities to either further maximize returns or mitigate risk.

• Prepare advanced financial analyses to assist senior management in the evaluation of various real estate decisions at different stages throughout real estate development cycle.

• Conduct budget-to-actual variance analysis for existing projects; ongoing budget management; in-depth understanding of costs incurred vs. cost to complete. Creating cash flow models, sensitivity tables, rent roll analyses, joint venture waterfall models, and other financial analyses required to evaluate and pursue acquisition opportunities.

• Review and critically analyze progress draw reports.

• Perform an active and critical role in the construction financing stage of each project.

• Maintain project files and follow-up on all necessary correspondence and communications.

• Prepare and present updated financial projections and executive reports to the executive team.

• Support and mentor junior team members.

Requirements:

• Must have a minimum of four years of relevant real estate development experience

• Minimum of a bachelor's degree in business / finance, economics, engineering or related field.

• A strong understanding of the full lifecycle of development from acquisition to approvals, unit sales, financing, construction, home closings and disbursements.

• Experience conducting financial analysis for development projects using advanced models in MS-Excel.

• Strong understanding of and ability to interpret, analyze and challenge project budgets and pro formas (experience analyzing financial statements is an asset).

• Experience developing and maintaining budgets, project pro formas, cash flow projections and financial reports.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Finance Controller

Brampton, ON - 5 days/week in office

$150,000–$175,000 base plus bonus and great benefits

We are recruiting for a Finance Controller to join a well-established international manufacturing company with operations in Brampton. This is a key leadership position, responsible for the full finance and accounting function of the Canadian business and contributing to the overall strategy and performance of the site. The business is currently around $25M annual revenues with realistic goals of getting to $100M within 4 years. They have already achieved this in another country and will aim to achieve the same in North America

Responsibilities:

• Oversee all core accounting operations, including billing, A/R, A/P, G/L, inventory/cost accounting, and revenue recognition

• Lead budgeting, forecasting, and month-end close processes

• Prepare and present monthly financial reports and variance analysis

• Support the plant management team in operational decision-making through financial analysis and performance reporting

• Ensure compliance with Canadian GAAP and internal financial controls

• Work closely with global finance teams on process improvements and reporting alignment

• Manage product costing and provide insights to support pricing and margin decisions

• Lead and develop a small finance team, including training and performance management

• Coordinate with external tax consultants to ensure proper compliance and risk mitigation

Requirements:

• 5+ years of experience in a similar finance leadership role

• CPA designated completed

• Bonus points if you have previous audit firm experience (not mandatory)

• Strong knowledge of ASPE and Canadian regulatory requirements

• Experience with budgeting, forecasting, and financial analysis

• Product cost accounting experience is essential

• Experience with SAP CO-FI is an asset

• Strong communication, leadership, and team collaboration skills

Manager of Investment and Corporate Accounting

Markham, ON - onsite

$120,000-$130,000 base plus bonus

The Manager of Investment and Corporate Accounting is a vital member of the Corporate Accounting team, supporting the Director of Finance in managing investment and corporate accounting functions. This role involves close collaboration with executives and owners while overseeing the accounting, compliance, and tax strategy for family office investments. Additionally, the Manager will assist in financial reporting and tax compliance for various corporate entities.

Key Responsibilities – Investment Accounting

• Manage tax compliance, reporting, and planning for the investment portfolio, collaborating with external advisors to ensure compliance with tax regulations in Canada and the U.S.

• Monitor cash positions across various brokerage accounts and lines of credit, implementing best practices for efficient cash management.

• Reconcile accounting records with external investment statements, capital account statements, and transaction histories on a regular basis.

• Oversee the accounting for the investment portfolio of the investment division and family foundation, covering publicly traded securities, derivatives, venture capital investments, and private equity funds across Canada, the U.S., and globally.

• Ensure the accurate and timely recording of investment transactions, including capital calls and distributions for private equity funds, while maintaining detailed monthly investment tracking reports.

Key Responsibilities – Corporate Accounting

• Assist in the preparation and review of the month-end closing and financial statements for various corporate entities.

• Support tax compliance efforts, including the preparation and/review of corporate tax returns and filings for relevant entities.

• Collaborate with external accountants to ensure all timely completion of the year-end audit and review; servicing as the primary liaison with external accountants on certain corporate entities.

• Other ad-hoc tasks as required and assigned.

Qualifications

• Bachelor's degree in accounting, finance, or a related field; CPA or equivalent designation preferred; CFA (or in progress) is an asset.

• Minimum 4 to 5 years’ experience, a good understanding of private equity investments and their tax implication is strongly preferred.

• Strong computer skills, specifically in Excel with strong proficiency in developing templates.

• Excellent communication and organizational skills, with the ability to collaborate effectively with internal teams and external advisors.

If you are interested in this position please contact and send your resume to Casey@winchesters.ca

Financial Controller

Mississauga, Ontario

$110,000-$130,000 base plus bonus and great benefits

Our client is a stable and growing real estate company in Mississauga, looking for a Financial Controller.

Our stable and experienced client is located in Mississauga and is looking for a financial controller to join the business who has more than just strong accounting experience. The business has been going through an exciting transformation as they streamline processes, go more paperless and improve/automate processes across the accounting department. The Financial Controller will manage the accounting and control functions, reporting the results of operations, while implementing these new changes across the department. The Controller will also be responsible for annual financial statements and tax returns for 100+ legal entities, investor reporting, cost controls, financial and cash planning along with financial/tax audits.

Responsibilities:

• Lead all day-to-day accounting operations and supervise staff members, including updating accounting records, monitoring bank accounts, completing monthly reconciliations, AP, AR, Payroll, General Ledger, Cost Ledger, etc.

• Assist with projects’ financing and prepare application package.

• Prepare the annual corporate budget in consultation with the CFO.

• Recommend and prepare documentation for distributions and investment of excess funds.

• Maintain company bank accounts ensuring all transactions are appropriate.

• Create and maintain cash flow forecast to ensure financing needs are met.

• Establish financial statement reporting timelines and supervise implementation.

• Implement and maintain a robust internal control system.

• Prepare monthly, quarterly and annual financial reporting package in accordance with ASPE.

• Assemble information for and liaise with external auditors.

• Oversee preparation and review of all tax filings and returns to ensure compliance with tax legislation, HST, CPP, EI, EHT, WSIB, T2, T5013, etc.

• Document and maintain complete and accurate supporting information for all financial transactions.

• Develop and maintain financial accounting systems for cash management, accounts payable, accounts receivable, credit control, and petty cash.

• Reconcile bank accounts. Review monthly results and prepare monthly variance reporting. Manage the cash flow and prepare cash flow forecasts.

• Prepare board materials including summarizing financial information, trend and variance analysis and summarize key performance indicators.

• Oversee and review interim and final closing and cash distribution to JV partners and investors.

• Develop and manage an effective costing system for the projects.

• Prepare Tarion related application and reports: vendor/builder registration, units’ enrollments, annual renewal, etc.

Requirements:

• Degree or diploma and CPA designation completed

• A minimum of 5 years of relevant experience

• Supervisory experience over at least 3 individuals

• Real estate and construction industry experience would be an asset but is not mandatory

• Strong background with internal controls

• Proficiency in MS Office, including Word, Excel and Outlook

• Ability to communicate effectively, both verbally and in writing

If you are interested in learning more about this opportunity, please apply now by sending your reume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller – Real Estate

Toronto, ON - In-office role to start and then will move hybrid

$110,000-$125,000 base plus 15% bonus and great benefits

We are working with a growing private equity company that’s looking for a Financial Controller to join their small and dynamic team. This business is in growth mode, acquiring stand-alone commercial properties across North America, with significant backing and a clear path for long-term expansion. Ideally you will join from a similar type of company (private equity or real estate related).

This role will be instrumental in building the finance and administrative infrastructure from the ground up, with the assistance of a great CFO. A key focus in the first year will be leading the transition away from a temporary support arrangement currently in place with a partner organization, and taking full ownership of the finance function.

This is a fantastic opportunity for someone who thrives in an exciting entrepreneurial environment and wants to be part of building something meaningful from the ground up.

Key Responsibilities:

• Lead all day-to-day accounting, accounts payable, and treasury operations

• Oversee financial reporting, budgeting, forecasting, and variance analysis

• Implement ERP systems and establish property-level accounting/reporting practices

• Develop internal controls and financial policies to support scale and compliance

• Manage relationships with external service providers (audit, tax, etc.)

• Support onboarding and integration of newly acquired properties

• Assist in financial due diligence and support M&A activity

• Collaborate with the executive team on financial strategy and planning

• Work with IT and other departments to streamline processes and improve access to financial data

• Ensure all statutory reporting, audit, and regulatory filings are completed accurately and on time

What We’re Looking For:

• Strong technical accounting experience with the ability to lead a full finance function

• Experience implementing systems, controls, and processes in a growing company

• Background in real estate, infrastructure, or other asset-heavy industries is preferred

• Comfortable working in a lean, entrepreneurial environment

• Excellent communicator and relationship-builder

• High integrity and emotional intelligence

• French fluency is a nice to have

If you are interested in learning more about this opportunity, please apply now by sending your reume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Manager, Finance and Accounting

North York – In office 5 days per week

$110,000–$125,000 base salary

Full-time – 12 to 18 month contract

We’re recruiting for a Finance & Accounting Manager to join a growing real estate investment company in North York. This is a demanding and fast-paced role that requires someone with strong technical skills, leadership ability, and a sharp eye for process improvements. You’ll be managing a small accounting team and working closely with leadership on reporting, audits, budgets, and financial analysis. This role is fully on-site and will require longer hours at times, so it’s best suited to someone who enjoys rolling up their sleeves and taking ownership of complex accounting work.

What you’ll be doing:

• Managing and reviewing monthly financial packages from third-party property managers

• Preparing quarterly reporting for a portfolio of multi-residential assets

• Reviewing monthly variance analysis on commercial and residential properties

• Supporting the annual budget process and preparing CAM/tax reconciliations

• Overseeing year-end working papers and liaising with auditors

• Leading and mentoring a small accounting team

• Improving accounting templates, reporting processes, and financial systems

• Supporting the Controller with special projects and system upgrades

What we’re looking for:

• 5+ years of progressive accounting experience

• Experience in real estate (multi-residential and/or commercial) preferred

• CPA or CPA-eligible strongly preferred

• Proficiency in Excel; Yardi experience is a bonus

• A proactive mindset and strong attention to detail

• Able to work independently in a fast-paced, high-expectation environment

If you are interested in learning more about this opportunity, please apply now by sending your reume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Finance Manager – Real Estate

$95,000–$110,000 + Bonus + Excellent Benefits

Downtown Toronto, ON | onsite

We are recruiting for a Finance Manager to join a highly respected real estate investment and asset management firm with a portfolio of prestigious assets in downtown North America. This is a fantastic opportunity for someone with a strong audit firm background or real estate private equity / asset management background — who wants to step into a high-profile, visible role working closely with the VP of Finance and senior leadership.

This position offers strong career development, exposure to investor relations, and the chance to work on a premier portfolio.

Responsibilities:

• Prepare and review monthly and quarterly IFRS-based financial forecasts

• Analyze cash flow projections for a range of properties

• Assist with annual business plans, budget packages, and valuation projections

• Review monthly co-ownership financials and support quarterly reporting cycles

• Develop management presentations and financial analysis for senior stakeholders

• Monitor and ensure compliance with loan covenants and reporting requirements

• Partner with asset management, leasing, marketing, and investor relations teams

• Support the month-end close process alongside the accounting team

• Lead or contribute to special projects and ad hoc financial analysis

Requirements:

• 3-5+ years of progressive experience in audit, accounting, reporting, finance, or FP&A

• Experience in real estate strongly preferred 

• CPA designation is an asset or pursuing

• Strong communication, organization, and analytical abilities

• Comfortable working in a high-performance, fast-paced environment

This role is based out of stunning downtown offices, and offers 4 weeks of vacation to offset longer hours at times. You’ll be part of a collaborative and driven finance group, with lots of opportunity to grow within a top-tier real estate platform. This is the type of company you join in this position and within a few years, you will be a Director or VP Finance.

If you are interested in learning more about this opportunity, please apply now by sending your reume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Controller

Brampton, Ontario - onsite

$130,000-$150,000 base, bonus and health/dental benefits

Our client is a growing and established manufacturing company and due to dramatic growth, they are looking to hire a Financial Controller to lead their accounting/finance team. This is a newly created position as most of these functions are currently outsourced. As a key member of the company’s Management Team, the Financial Controller will lead and be responsible for the daily administration of the company’s accounting and financial activities, reporting directly to the owner and supervising a small team of junior accountants. The business is currently $25M revenue but plan to get up to $100M within 4 years.

This is an excellent opportunity for a designated CPA Financial Controller coming from manufacturing who has some experience supervising a small team and wants to help this company move through all the growing pains that come with dramatic expansion. The position will allow the Financial Controller to have a broad focus versus a narrow one with a larger organization. We are looking for an individual who can lead by delegating responsibilities but also take a hands-on approach by rolling up the sleeves if and when necessary. Apply now – this owner is motivated to hire sooner rather than later.

Responsibilities

• Oversee all financial operations of the company including subsidiaries.

• Manage any third parties to which accounting or finance functions have been outsourced.

• Monitor and direct the implementation of strategic business plans.

• Manage the capital request and budgeting processes.

• Develop financial and tax strategies.

• Participate in key decisions as a member of the executive management team.

• Supervise and assist with negotiating acquisitions.

• Oversee the issuance of all financial information.

• Understand and mitigate key elements of the company's risk profile.

• Ensure that record-keeping meets the requirements of auditors and government agencies.

• Maintain relations with external auditors and investigate their findings and recommendations.

• Monitor cash balances and cash forecasts.

• Represent the company with investment bankers and investors.

• Provide monthly, quarterly and annual in-depth reporting and data analysis of all company related income and revenue statements.

• Responsible for creating, allocating and monitoring all company’s budgets.

• Direct management responsibility for all accounting departments.

Requirements

• CPA designation

• Proven experience as an Accounting Manager or Controller in Manufacturing

• Excellent leadership, communication and organizational skills

• Positive and professional demeanor

• Proficient in Microsoft Office

• Must have the ability to maintain the highest degree of integrity and confidentiality.

If you are interested in learning more about this opportunity, please apply now by sending your reume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Manager, Finance – Real Estate Private Equity

Downtown Toronto -

$110,000–$120,000

We’re recruiting for a fantastic opportunity with a leading real estate private equity company in downtown Toronto. This organization is known for its world-class portfolio, strong performance, and exceptional internal talent. They’re looking for a skilled CPA with real estate or asset management industry experience to step into a Manager-level finance role supporting North American investments.

This position sits on the corporate finance team and is responsible for a range of high-impact functions including fund reporting, investment onboarding, debt management, investor communications, financial analysis, and more. It’s a broad role with great visibility and exposure to senior stakeholders, ideal for someone looking to deepen their expertise in real estate private equity.

What you’ll be doing:

• Overseeing financial and management reporting for real estate investments (IFRS and US GAAP)

• Preparing investor materials, board packages, valuations, and capital call/distribution schedules

• Managing the debt lifecycle including funding, payments, compliance, and lender reporting

• Collaborating with tax, asset management, and capital markets teams

• Leading and mentoring a small team of finance professionals

• Supporting audits, SOX controls, and continuous improvement of financial processes

What we’re looking for:

• CPA designation (CA preferred)

• Several years of progressive experience in accounting and finance, with a mix of public accounting and industry

• Strong technical knowledge of IFRS 

• Experience managing a team

• Excellent Excel skills and the ability to communicate clearly and confidently

This is a rare chance to join a highly respected platform and work with some of the best minds in the business. If you enjoy complex transactions, real estate finance, and want a seat at the table for major deals, this role is for you.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Corporate Accountant 

Downtown Toronto, ON (Hybrid)

$85,000–$95,000 base + bonus and excellent benefits

We are recruiting for a Senior Corporate Accountant to join a dynamic and collaborative accounting team in a downtown Toronto office. This is a great opportunity for someone with strong full-cycle accounting experience looking to grow within a high-performing environment.

Responsibilities:

• Prepare journal entries, account reconciliations, and working papers

• Handle intercompany loans, distributions, equity, and debt transactions

• Complete month-end close including accruals, prepayments, amortization, and bank reconciliations

• Assist with quarterly and annual financial statements

• File HST returns and assist with tax and audit requests

• Participate in the budgeting process and variance analysis

• Identify opportunities for process improvement

• Support special projects as needed

Requirements:

• 3+ years of relevant corporate accounting experience

• CPA designation (or near completion) preferred

• Strong Excel skills

• Detail-oriented with excellent analytical and communication skills

• Comfortable working with cross-functional teams and meeting tight deadlines

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Finance Controller

Brampton, ON - 5 days/week in office

$150,000–$175,000 base plus bonus and great benefits

We are recruiting for a Finance Controller to join a well-established international manufacturing company with operations in Brampton. This is a key leadership position, responsible for the full finance and accounting function of the Canadian business and contributing to the overall strategy and performance of the site. The business is currently around $25M annual revenues with realistic goals of getting to $100M within 4 years. They have already achieved this in another country and will aim to achieve the same in North America

Responsibilities:

• Oversee all core accounting operations, including billing, A/R, A/P, G/L, inventory/cost accounting, and revenue recognition

• Lead budgeting, forecasting, and month-end close processes

• Prepare and present monthly financial reports and variance analysis

• Support the plant management team in operational decision-making through financial analysis and performance reporting

• Ensure compliance with Canadian GAAP and internal financial controls

• Work closely with global finance teams on process improvements and reporting alignment

• Manage product costing and provide insights to support pricing and margin decisions

• Lead and develop a small finance team, including training and performance management

• Coordinate with external tax consultants to ensure proper compliance and risk mitigation

Requirements:

• 5+ years of experience in a similar finance leadership role

• CPA designated completed

• Bonus points if you have previous audit firm experience (not mandatory)

• Strong knowledge of ASPE and Canadian regulatory requirements

• Experience with budgeting, forecasting, and financial analysis

• Product cost accounting experience is essential

• Experience with SAP CO-FI is an asset

• Strong communication, leadership, and team collaboration skills

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Investment Analyst

North York, Ontario (5 days/week in office)

$75,000–$95,000 base plus bonus

We are recruiting for an Investment Analyst to join a busy and growing investment team in North York, ON. This role offers hands-on exposure across the full investment lifecycle—acquisitions, financing, analysis, and asset management—primarily focused on the multifamily real estate sector. It’s a great opportunity for someone who enjoys financial modeling, transaction execution, and working closely with senior decision-makers. 

Responsibilities:

• Prepare detailed investment and financial analysis to support due diligence on new acquisitions, with a focus on multifamily real estate

• Develop and maintain financial models to evaluate deal performance and support investment recommendations

• Assist in acquisitions and financing activities, including tracking the deal pipeline, managing transaction summaries, and preparing pro formas and budgets

• Create financing decks and confidential information memorandums (CIMs) for lenders and internal stakeholders

• Work with property managers to support day-to-day asset management and identify strategies to optimize portfolio cash flow, reduce vacancies, and manage unit turnovers

Requirements:

• 1–3 years of experience in real estate investment, corporate finance, or a similar analytical role

• Strong financial modeling skills and familiarity with real estate pro formas

• Proficiency in Excel and PowerPoint

• Strong communication and project coordination skills

• A degree in finance, accounting, economics, or a related field

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Financial Analyst

North York, ON (on-site, 5 days/week)

$90,000–$110,000 base + bonus

We are currently recruiting for a Senior Financial Analyst to join a well-established, growing real estate investment firm with a strong portfolio of multi-family properties. This is a full-time, in-office role based in North York, working in a smaller, collaborative office environment.

The role will focus on budgeting, forecasting, and financial analysis for a growing portfolio of income-generating residential assets. There will be plenty of opportunity to work on interesting ad hoc projects and contribute to ongoing improvements across finance and operations. The ideal candidate is someone with a strong foundation in accounting/finance, excellent EXCEL skills, and a genuine interest in real estate.

Key Responsibilities:

• Prepare and manage annual budgets and reforecasts for multi-family properties

• Perform monthly and quarterly financial analysis to track performance and identify variances

• Support the development of financial models and reporting tools

• Partner with property management, operations, and asset management teams to gather data and provide insight

• Assist with internal reporting packages for senior leadership and investors

• Take on ad hoc projects across the broader finance function

Requirements:

• 4–6 years of relevant experience in accounting, finance, or real estate

• Strong experience with budgeting, forecasting, and financial analysis

• Advanced Excel skills; experience with Yardi or similar systems is an asset

• CPA designation (or in progress) is preferred but not required

• Excellent attention to detail and a collaborative mindset

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Bookkeeper
Concord, Ontario – onsite
$60,000-$75,000, no bonus, but great benefits paid by the company

Our client is a real-estate company based in Concord, Ontario. They are looking for a passionate bookkeeper to join the team on a full-time basis. This position offers an excellent opportunity to work in a company that manages a diverse real estate portfolio while being a key member in the business. The business has been around for several decades and offers excellent work/life balance.

The successful candidate will be a responsible for providing timely and accurate management reporting for commercial and residential real estate.

Responsibilities:

• Handle day-to-day accounting duties including Accounts Receivable, booking journal entries, banking (including making deposits), reconciling bank accounts and preparation of HST returns;

• Ensuring accuracy of tenant’s ledger and the timely resolution of receivable or billing differences;

• Assist Property Management and other departments as requested with providing accurate/timely accounting information;

• Liaise with property accountants or other counterparts in respect of various accounting, reporting, and property management activities;

• Provide assistance in dealing with tenant enquiries;

• Other projects as required.

Requirements:

• Post-secondary accounting education or equivalent accounting qualification

• Proficient in Excel, Microsoft Word, and accounting software packages

• Good communication and relationship building skills – both written and verbal

• Good attention to detail

How to Apply

We would like to thank all applicants for your interest in working as part of our team. Please send all job applications to laikyn@winchesters.ca Only those applicants selected to move forward in the recruitment process will be contacted.

Manager, Investment and Corporate Accounting
Markham, ON – onsite
$100,000-$120,000 base plus discretionary bonus and great benefits

Are you an experienced accounting professional with a passion for investment and corporate accounting? This is your chance to join our client which is a growing family office, working closely with the executives and owners to oversee critical financial operations and lead tax and compliance strategies for their diverse portfolio.

The Role

As the Manager, Investment and Corporate Accounting, you will report to the Director of Finance and play a pivotal role in managing the accounting for the Group’s family office investments and corporate entities. This position requires a highly organized professional with strong technical expertise in investment and corporate accounting.

Key Responsibilities

• Oversee accounting for the Group’s investment portfolio, including publicly traded securities, derivatives, venture capital, and private equity fund investments across Canada, the US, and globally.

• Ensure the accurate and timely recording of investment transactions, including capital calls and distributions for private equity funds.

• Prepare and maintain monthly investment tracking reports.

• Reconcile accounting records with external investment statements, capital account statements, and transaction histories.

• Monitor cash positions in brokerage accounts and lines of credit to ensure optimal cash management.

• Lead tax compliance, reporting, and planning for the investment portfolio in collaboration with external advisors, ensuring compliance with Canadian and US regulations.

• Assist in preparing and reviewing month-end closings and financial statements for the Group’s corporate entities.

• Support tax compliance efforts, including the preparation and/or review of corporate tax returns and filings.

• Collaborate with external accountants to ensure timely completion of year-end audits, serving as the primary liaison for specific corporate entities.

• Handle ad-hoc tasks and projects as required.

About You

• Education: Bachelor’s degree in accounting, finance, or a related field. CPA designation preferred; CFA (or in progress) is an asset.

• Experience: Minimum of 4-5 years’ experience with a solid understanding of private equity investments and their tax implications.

• Skills: Proficiency in Excel with a proven ability to develop templates and models, along with excellent organizational and communication skills.

• Attributes: Detail-oriented, proactive, and comfortable collaborating with internal teams and external advisors.

Why Join this company?

This is more than just a role; it’s an opportunity to contribute to a thriving organization while developing your expertise in investment and corporate accounting. You’ll work in a dynamic, collaborative environment that values innovation and excellence.

Interested? If this sounds like the right fit for you, please apply now to Casey La Russa.

Vice President, Finance
Welland, Ontario – hybrid
Competitive base plus bonus and benefits

Join a growing company dedicated to excellence in their multiple service lines. We are seeking an individual who wants to join a fast-growing and dynamic group of companies with a head office in Welland, ON. The company’s top line revenue has grown tremendously over the past few years. The VP Finance will be instrumental to lead the finance and accounting team and provide strategic oversight to the company’s financial operations. You will report directly to the President of the company with a small accounting and finance team.

Responsibilities:

• Manage all QuickBooks accounting for several manufacturing plants

• Handle daily sales reports, journal entries, payables, and bank reconciliations

• Monitor cash flow and prepare monthly P&L reports

• Manage quarterly WSIB and HST filings

• Oversee accounting for multiple four different entities unrelated to the manufacturing business lines

• Issue monthly rent invoices, handle mortgage payments, and bank reconciliations

• File quarterly HST returns

• Oversee bank reconciliations, intercompany invoicing, inventory adjustments, and month-end closes for parent company

• Handle payroll for multiple divisions and process cash receipts

• Submit covenant calculations to the bank and manage accounts receivable insurance

• Prepare working paper files for year-end, maintain fixed asset subledgers, and process T5s

• Analyze and manage Visa statements for employee charge approvals

Qualifications:

• Undergraduate degree in Accounting, Finance, Business, or related discipline, with a Chartered Professional Accountant (CPA) designation

• Intermediate to advanced proficiency in Microsoft Office, with the ability to present data and findings effectively.

• Self-starter with strong motivation to take ownership of tasks, while also excelling in a team environment.

• Strong ability to manage multiple priorities in a fast-paced environment.

• Ability to work extended hours to meet tight deadlines

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Manager, Land Development Accounting

North York (In-office role)

$100k – $110k plus discretionary bonus and benefits

Our client, a leader in land development, is seeking a Manager, Land Development Accounting to join their team. The successful candidate will oversee financial operations for a diverse portfolio of land development projects, providing key insights and leadership.

Responsibilities:

• Oversee accounting and financial operations for assigned portfolios, including land purchase and sales, cost recoveries, trial balance reviews, account reconciliations, and job costing.

• Provide accurate and timely monthly, quarterly, and annual reporting, including variance and cost analysis for Senior Management and Project Managers.

• Prepare and maintain detailed project budgets in collaboration with Project Managers and the Finance Team, focusing on construction costs and fee analysis.

• Monitor and manage cash flow for development projects, including cash flow forecasting, funding draws, and loan utilization.

• Review invoices, manage change order processing, and oversee invoice coding.

• Prepare and reconcile internal and external loans, including interest calculations.

• Supervise and provide oversight to the land development accounting team.

• Assist in year-end financial statement preparation in compliance with accounting principles and audits.

• Document and maintain accurate financial transaction records.

• Lead ad hoc projects and analyses to support company objectives.

Requirements:

• CPA designation

• Bachelor’s degree in business or accounting.

• Several years of experience in full-cycle accounting within land development or property accounting.

• Proficiency in cash flow analysis, budgeting, and understanding joint business arrangements (e.g., JVs, partnerships).

• Strong problem-solving skills with attention to operational and financial impacts.

• Advanced proficiency in Microsoft Office, particularly Excel

If you are interested in applying for this opportunity, please email your resume to laikyn@winchesters.ca. Due to the high volume of applicants, only those selected for interviews will be contacted.

Junior Accountant
North York (In-office role)
$60k – $70k plus discretionary bonus and benefits

Our client, a leader in land development, is looking for a Junior Accountant to join their team. This role is ideal for someone highly motivated, detail-oriented, and ready to thrive in a fast-paced environment. The successful candidate will take on accounting tasks for a diverse portfolio of land development projects.

Responsibilities:

• Perform monthly bank reconciliations and manage accounts payable for multiple entities.

• Track and reconcile lot discharges, house closings, and loan balances with external statements.

• Set up and maintain accounts receivable invoices and process internal and external cash calls.

• Reconcile intercompany accounts and create/post journal entries.

• Prepare HST returns (monthly, quarterly, or annually).

• Manage and reconcile letters of credit for all projects.

• Maintain accounting records in compliance with Canadian GAAP and company policies.

• Support auditors with accurate and timely documentation.

• Participate in special projects and back charge processing.

Requirements:

• Bachelor’s degree in Business or Accounting; CPA designation or equivalent is an asset.

• 1-2+ years of experience in accounting

• Excellent communication skills and a collaborative team player.

If you are interested in applying for this opportunity, please email your resume to laikyn@winchesters.ca. Due to the high volume of applicants, only those selected for interviews will be contacted.

Portfolio Operations Manager
Toronto, ON – hybrid
Flexible compensation with huge upside

We are seeking a highly skilled and experienced Portfolio Operations Manager to help our client in managing a portfolio of a combined AUM of $100M for some prominent family offices. This role offers a unique opportunity to optimize operational processes, help an experienced portfolio manager, and work closely with top-tier family offices. Currently the wealth management firm is waiting to get approved by the OSC and this role will be pivotal to that. We are seeking someone with several years of experience working for an investment fund manager. We are also potentially open to individuals with a strong fund accounting background.

Key Responsibilities

• Manage investments across Fixed Income, Money Market, and Real Estate portfolios.

• Oversee and coordinate back-office administrative operations.

• Enhance efficiency by streamlining processes for fund mergers and closures, utilizing strategies such as weekly rebalancing, capital calls, and fund-of-funds (FOF) initiatives.

• Extract and analyze daily trade data using SQL to provide actionable insights for the Fund Accounting and Trading teams.

• Collaborate effectively with custodian banks, portfolio managers, and traders to resolve portfolio discrepancies and ensure smooth operations.

• Verify and report transactions, including domestic and foreign bond/equity purchases, derivative trades, term loans, and margin movements.

• Coordinate the settlement of Short-Term Notes (STNs) through close interaction with trading desks, brokers, and internal custodians

• Develop macros and automated tools to optimize workflows

Requirements:

• Designed and implemented process improvements, including automation of trade settlement workflows and enhanced client reporting templates.

• Successfully supported large-scale fund integrations and operational initiatives, contributing to the growth and efficiency of the portfolio management process.

• Proven experience in fund operations, portfolio management, or a similar role.

• Expertise in Bloomberg Terminal, SQL, and financial reporting tools.

• Exceptional organizational and problem-solving skills with a focus on process optimization.

• Adept at building relationships with internal and external stakeholders, including portfolio managers, custodians, and trading desks.

If you are interested in learning more about this opportunity, please apply now by sending your resume to laikyn@winchesters.ca Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Director of Finance – Accounting (12-18 month contract)
Downtown Toronto, ON – Hybrid
Competitive salary

We’re seeking an experienced Director of Finance to join a dynamic Toronto-based client. This role is pivotal in overseeing the financial reporting processes – monthly, quarterly, and annually – for the Core Accounting team. You’ll support operations, including acquisitions and dispositions, and play an integral role in working cross-functionally with senior leadership, investment, asset management, and property finance teams.

If you’re passionate about leadership, problem-solving, and continuous improvement, this role is tailored for you. We’re looking for a solutions-oriented, accountable team player who thrives in a fast-paced environment and enjoys mentoring and building cohesive teams.

Responsibilities:

• Lead monthly, quarterly, and annual reporting deliverables, ensuring accuracy, timeliness, and ASPE compliance for a portfolio of funds.

• Review and verify monthly forecasts to maintain compliance with covenants, manage liquidity, and provide accurate projections for acquisitions and dispositions.

• Oversee the quarterly board reporting process, ensuring all inputs are accurate for board presentations.

• Manage quarterly compliance reporting to lenders.

• Direct the annual budget process, validating the accuracy and reasonableness of all assumptions.

• Serve as the primary point of contact for the annual audit.

• Oversee investor transactions, including capital calls, returns, preferred returns, and gain distributions.

• Address investor inquiries promptly and professionally.

• Lead and mentor a team of four, providing guidance and fostering professional growth.

Requirements:

• Undergraduate degree in Finance or Business; CPA designation required.

• Real estate experience is a major plus.

• 8+ years of experience

• Supervisory experience

• Strong written and verbal communication abilities.

• Preference will be given to individuals with prior audit firm experience

• A collaborative team player with high ethical standards and integrity.

If you are interested in learning more about this opportunity, please apply now by sending your resume to katherine@winchesters.ca Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Corporate AP/AR Specialist
Located Mid-Toronto (4 days/week in office)
Salary between $60k – $65k plus discretionary bonus and benefits

Our real estate client is looking for a Corporate AP/AR Specialist to join their dynamic team to support with the day-to-day AP/AR functions and to contribute to the overall success of the team. 

Responsibilities:

• Match invoices to backup documents (e.g., pay orders, quotes, receipts, etc. and obtain proper approvals for invoices

• Monitor corporate invoice inbox and communicate with vendors in a professional manner

• Address any invoice discrepancies with the vendors 

• Reconcile vendor statements/ledgers to AP subledgers, research and correct discrepancies with analysts

• Process invoices into Yardi using the scanner/labeler. 

• Manage credit card reconciliations process with card users and prepare chargeback invoices as required

• Prepare fee billings for applicable entities in a timely manner.

• Process payments and cheque batches for controller review in a timely manner 

• Process payments and cheque batches for controller review in a timely manner

• Prepare deposits for bank using deposit scanner and prepare manual deposits as necessary. 

• Maintain files and documentation thoroughly and accurately 

• Assist with any inquiry by pulling copy of invoices as needed.

• Ensure all banks are reconciled on a weekly basis by clearing cheques, deposits and fees. Communicate when entries are missing

• Centralize all HST filings and payments for corporate entities through the online tax filing system monthly

• Direct chargebacks to other entities in the Group for payments processed directly by corporate.

• Liaise/coordinate with other inter-company AP contacts and vendors as required, and manage reconciliation processes for the Group

• Adhoc reports as required

Qualifications

• College degree in related field

• A minimum of 3 years experiences in accounts payable/ receivable functions.

• Experience using Yardi voyager

• Superior interpersonal and problem-solving skills, with a customer service focus. Portrays a

• professional image

• Detail-oriented, process-driven, and take responsibility for your work

If you are interested in applying for this opportunity, please email your resume to laikyn@winchesters.ca. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Senior Analyst – Real Estate Development
Toronto, ON – Hybrid
$80,000-$110,000 Base Plus Bonus and Great Benefits

Our client is a very active condo and rental development company. Reporting to the VP of Investments and Asset Management, this key member of the team will play a crucial role in evaluating potential investment opportunities and providing insightful analysis to support informed decision-making. This position involves project modelling, analysis, tracking, thorough industry research, analyzing financial data, assessing market trends to identify promising investment prospects and reporting on all aspects of the development process to the Management Team. This will also include asset management duties for a portfolio of development projects in the GTA.

Responsibilities:

• Gather and analyze financial statements, market data, industry reports, and other relevant information to assess investment viability in real estate development acquisitions

• Perform sensitivity analyses and scenario planning to evaluate the impact of market fluctuations and economic variables on investment performance

• Underwrite mid- and high-rise multifamily rental and condo development opportunities in the GTA

• Perform due diligence on potential investment targets, including evaluating financial performance, competitive positioning, and growth potential

• Financial modelling to forecast project budgets, equity requirements, and partnership returns for a portfolio of rental and condominium projects

• Collaborate with Development, Construction, and Finance teams in strategic planning, regulatory research, and budget monitoring throughout the project lifecycle

• Assist in capital raising/investor relations efforts through the preparation of investment materials, scenario analyses, investment reporting, and other ad hoc tasks as required

• Lead monthly investment accounting reconciliations, equity/debt draw requests and cost monitor budget reviews to ensure timely and effective project management

• Performed extensive financial modeling including cash flow projections, detailed development and rental proformas, DCF’s, capital structure optimizations, and equity waterfalls

• Prepare investment memos and reports outlining findings, analysis, and recommendations for investment opportunities.

Requirements:

• Minimum of 1-3 years of relevant experience with real estate finance, or development management

• Experience conducting financial analysis for potential land/real estate acquisitions using advanced models in MS-Excel

• Experience developing and maintaining budgets, project proformas, cash flow projections and financial reports

• Strong understanding of development financing (typical financing structures at various stages of development) and land economics.

If you are interested in learning more about this opportunity, please apply now by emailing resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Vice President Finance
North York, ON – Onsite
$180,000-$200,000 Base Plus Competitive Bonus and Great Benefits

 Due to the growth, our client is currently looking for a VP Finance to join the group in their North York office. Backed by private equity, this company is poised for serious growth provincially and nationally, eventually internationally. Their industry is one of Canada’s fastest growing sectors and for the right candidate, this position will catapult your career to become the CFO within the next few years. There currently is no CFO and as VP Finance, you will be number one for all finance/accounting related responsibilities. Reporting directly to the CEO, this new role has a wide mandate which requires an adaptable individual with a desire to create positive change, build and mentor teams, and grow the business in accordance with the company’s growth strategy.

The VP Finance will have primary responsibility for functions including corporate finance, accounting, treasury and FP&A as well as implementing and managing an internal control framework in line with the company’s strategic growth aspirations. This will include direct responsibility for: accounting, cash flow management, financial analysis, reporting, forecasting and planning, risk management, tax, controls and compliance, etc.

The company has posted positive growth year-on-year for the past eight years and over the next 5 years the CEO is looking to double the revenue through organic growth and by opening new sites. This position is not a 9-5 role, but will offer the successful candidate a true seat at the table with the ownership and will eventually offer an excellent LTIP with excellent growth potential.

Responsibilities:

• Work with the CEO to develop and implement a financial strategy and overall strategic plan for the company

• Serve as a leader in the organization (Supervisor, Motivator and Mentor)

• Review all required reporting for Senior Management while liaising with external auditors

• Monthly, quarterly and annual management, financial and tax reporting

• Monitor key performance indicators and recommend and implement improvements

• Report financials to the board of directors on a quarterly basis

• Work closely with legal to support the documentation and review of legal documents, including contracts, agreements, acquisition documents, and other documents

• Review the maintenance of budgets and financial forecasting models

• Maintain and review tax strategy, internal controls and compliance functions

• Develop and maintain relationships with relevant external service providers (Banks, External Auditors, CRA and Consultants)

Requirements:

• 10+ years of experience

• Bachelor’s degree in business or a related field along with CPA certification

• Ideally previous experience in an audit firm

• Proven track record of creating/improving accounting functions and building accounting systems and processes

• Strategic thinker capable of coming up with financial solutions that are supportive of the company’s strategy

• Demonstrated success in establishing cooperative working relationships both internally and externally

• Strong verbal and written communication skills

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Senior Corporate Accountant Downtown Toronto, Hybrid (3 Days a Week in Office)$95,000 – $110,000 Base +  Bonus 

Our client, a fast-growing real estate developer, is looking for a Senior Corporate Accountant to join their team. They are looking for someone who thrives in a changing environment, has a willingness to learn and who can think on their feet. You will regularly be dealing with JV partners and external stakeholders so strong communication skills and a mature personality will be required. They are offering a very competitive salary with great benefits and growth opportunities. Bonus points if you have experience with investor reporting.

Responsibilities:

• Responsible for day-to-day accounting for investment activities for entities withing the organizational structure

• Monthly, quarterly and yearly financial reporting for investors including reviewing trial balances, preparing adjusting journal entries and working paper files and preparing financial statements required for internal and external purposes, compliance and tax filings

• Oversee legal documentation internal filing to ensure completeness and legal organizational chart is updated

• Prepare analytical review of performance of consolidated results to communicate with investors

• Organize and maintain reporting deadlines across all entities across the company

• Ensure compliance for tax, debt and other commitments are met for various entities

• Work with various teams to ensure deadlines and results that consolidate into corporate and investor financials are communicated

• Communicate with third parties on any inquiries about financial results

• Maintain strong stakeholder relationships by understanding needs and upholding the company values in providing value to them

Requirements:

• CPA designation or pursuing a CPA designation

• Bachelors in Finance or Accounting degree is required

• Corporate accounting experience required with financial statement preparation

• Advanced Excel skills

• Sound analytical and quantitative skills, rigorous attention to detail

• Entrepreneurial spirit, driven to create sound and efficient procedures

• Excellent verbal and written communication skills, listening skills and organizational skills

• Ability to multi-task, prioritize and follow written and verbal instructions

If you are interested in learning more about this opportunity, please apply now by emailing resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Senior Project Accountant
Toronto, ON
$75,000 – $95,000 Base Plus Bonus, Excellent Benefits 

About the Job

Mid-sized architecture and design firm, located downtown Toronto with beautiful offices.

Our industry-leading client provides superior professional services and this role is pivotal to the operations of the Toronto office. The senior project accountant will be responsible for the accurate and timely general accounting of multiple or complex projects.

Responsibilities:

• Prepare monthly invoices, budgets and project management reports.

• Provide accurate and timely accounting, reporting and project information for assigned projects.

• Set up and maintain projects on an in-house accounting system according to contract terms.

• Track and input budget data for assigned projects.

• Prepare, code and input project invoices.

• Answer inquiries from staff, vendors or clients, and communicate financial information to project managers.

• Maintain accounting files.

• Make calls to clients to follow up on accounts receivable.

• Input and post consultant invoices, communicate with consultants and organize their payments.

• Review project contracts and additional service requests to understand the financial requirements on each project.

• Analyze project cost reports and meet frequently with the Business Manager and Project Managers to review status of projects for invoicing, profitability, earnings, costs, and cash flow.

• Understand how projects earn revenue in the accounting system and assist the Business Manager monthly in analyzing and recording monthly project earnings.

• Work independently to research and resolve financial issues.

• May provide accounting support to other staff as needed.

• May educate and/or guide non-financial staff on accounting procedures.

• Take personal responsibility for fostering a green workplace through sustainable work practices.

Requirements:

• Bachelor’s degree in accounting and 3+ years accounting experience; or an equivalent of education and experience required.

• Accounting experience in a project-based business preferred.

• Knowledge of accounting and finance principles and practices, and the analysis and reporting of financial-related reports.

• Proficiency in MS Office, including Word, Excel and Outlook.

• Ability to communicate effectively, both verbally and in writing.

If you are interested in learning more about this opportunity please visit our website or email resume to laikyn@winchesters.ca to apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Manager Fund Accounting and Reporting
Toronto, Ontario – Hybrid and flexible work environment
$130,000-$145,000 base plus bonus and excellent benefits

With this company being one of the fastest growing real estate companies in Canada you will get experience and insight into the multifaceted operations and execution of high-profile real estate IPP and development projects. The company is looking to build a brand-new fund and will need your help. You will join and be responsible for fund financial reporting for internal and external purposes, full-cycle fund accounting, monitoring and management, related investor calculations and reporting. You will also help support tax and debt compliance across the organization. By the end of the year, you will be able to hire one individual underneath you and really drive change/process improvement within the division.

We are looking for someone who has a strong financial reporting background at either an investment manager or REIT. If this is you, please apply now.

Responsibilities:

• Lead all finance, accounting and financial reporting matters relating to the fund

• Responsible for day-to-day accounting for investment activities for entities within the fund organizational structure

• Monthly, quarterly and yearly financial reporting for investors, including calculating NAV, reviewing trial balances, preparing adjusting journal entries and working paper files and preparing financial statements required for internal and external purposes, compliance and tax filings

• Support the creation of procedures and internal standards for Investor and fund reporting

• Maintain strong stakeholder relationships by understanding needs and upholding the company’s values in providing value to them

• Prepare analytical review of performance of consolidated results to communicate with investors in collaboration with Investor Relations

• Communicate with investors on attribution and other inquiries about fund financial results in collaboration with Investor Relations

• Organize and maintain reporting deadlines across all fund entities within the company’s ecosystem

• Oversee legal documentation internal filing to ensure completeness and legal organizational chart is updated

• Manage compliance for tax, debt and other commitments for all fund various entities

• Work with various teams to manage deadlines relating to results that consolidate into fund financials and investor reports

• Over time, help to recruit, train and develop additional staff within the fund / portfolio pillar of the Accounting and Operations team

Requirements:

• CPA designation

• Bachelor’s degree in Commerce, Business Administration, Finance, or Accounting

• A minimum of 3 years of fund or REIT accounting experience, including financial statement preparation and NAV calculations with IFRS experience preferred

• Commercial Real Estate experience

• Sound analytical and quantitative skills, rigorous attention to detail

• Entrepreneurial spirit, driven to create sound and efficient procedures that help build and scale the organization

• Excellent oral and written communication skills, listening skills and organizational skills

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

VP Finance
Downtown Toronto, ON – Will Begin In Office and Move to Hybrid After Several Months
$130,000 – $150,000 Base Plus a $50,000 Target Bonus, Excellent Benefits & Vacation

Our client is a professional services firm that offers accurate, effective accounting and finance services at a reasonable cost, providing their clients the peace of mind in order to focus on core matters within their business. As VP Finance you will help manage and offer services which include CFO functions, controllership and bookkeeping, and financial admin. Their clients include small and micro-cap public companies with operations, capital pool companies, Canadian or U.S. publicly listed shell entities with no operations, private entities growing quickly or looking at acquisitions or divestitures, and private entities preparing to go public and private companies staying private.

The VP Finance will act as Chief Financial Officer (CFO) for both internal and external clients. You will provide both operational support and lead the financial reporting function at these organizations. You will supervise the finance unit and will act as the chief financial spokesperson for the organization. The VP Finance will report directly to the President/Chief Executive Officer (CEO) and directly assists on all strategic and tactical matters.

RESPONSIBILITIES

• Participate in the development of new business initiatives by assisting the CEO in identifying potential clients, preparing proposals, and evaluating the cost-effectiveness of proposed service delivery.

• Ensure the implementation of adequate controls and the availability of supporting documentation to facilitate successful independent and governmental audits of all purchases.

• Assist in overseeing clients’ financial activities to ensure compliance with IFRS, US GAAP, and other relevant financial reporting standards, as well as federal, provincial, local, and contractual guidelines. This includes interpreting regulations, disseminating government requirements to relevant personnel, and monitoring compliance.

• Establish and maintain internal control systems to safeguard clients’ financial assets and ensure the preparation of annual financial statements adheres to regulatory requirements.

• Participate in Board and Subcommittee meetings, including presenting financial information to the Audit/Finance Committee.

• Provide training to the Finance Unit staff, including bookkeepers and controllers, to enhance their understanding of financial management.

• Oversee the production of monthly financial reports and statements tailored to the needs of Executive management, the Audit/Finance Committee, and the Board of Directors.

• Stay abreast of advancements in financial accounting and reporting technologies and assist with their implementation when necessary.

• Take on additional responsibilities related to clients’ financial reporting processes and internal matters as needed.

Qualifications

• 10-12+ years of professional experience, including experience with public company audits, with preference given to candidates with experience at an audit firm.

• Accounting designation (CPA)

• Demonstrated experience in financial management and accounting, ideally in the North American public company sector and involvement in creation of the financial statements.

• Proven effectiveness leading a team of accounting staff.

• Technologically savvy, with an ability to use systems to create organizational efficiencies.

• Flexible and a self-starter; able to multi-task while also being highly detail-oriented.

If you are interested in learning more about this opportunity, please apply now by emailing resume to elan@wincesters.ca Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Director of Mortgage Origination
Calgary, Alberta – hybrid
$300,000-$600,000 (base + bonus) plus excellent benefits

Are you an experienced commercial real estate professional with a passion for structuring innovative mortgage solutions? We are looking for a Director of Mortgage Origination to join a high-performing team in Western Canada. This is an exciting opportunity to contribute to a growing portfolio of mortgage investments while leveraging your deep knowledge of real estate markets across Canada.

As a Director, your focus will be to identify, structure, and manage mortgage investment opportunities. You’ll work closely with brokers, developers, and lenders to build a robust pipeline while overseeing detailed analysis and presenting opportunities to an investment committee.

Responsibilities

• Build and maintain a strong pipeline of mortgage investment opportunities aligned with the company’s objectives.

• Develop and nurture relationships with industry stakeholders, including brokers, developers, and service providers.

• Conduct preliminary reviews, site visits, and due diligence for potential investments.

• Recommend deal structures, negotiate term sheets, and lead the preparation of investment proposals.

• Present and advocate for investment opportunities at committee meetings.

• Collaborate with underwriting teams to structure and close transactions while adhering to policies.

• Represent the organization at industry events and conferences to strengthen market presence.

• Act as a resource to identify and refer opportunities across various product lines within the organization.

What You Bring

• 7-10 years of experience in commercial real estate, ideally in an origination or similar role.

• A university degree in business or a related field.

• Expertise in real estate investment analysis, financial structuring, and transactional risk management.

• Strong negotiation, critical thinking, and communication skills.

• Familiarity with complex lending agreements and the ability to navigate financial and contractual challenges.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted. 

Project Accountant
Toronto, Ontario – hybrid
$75,000-$85,000 annual salary, 3 weeks of vacation, great health/dental benefits

Our client is a well-respected real estate company that is heavily involved in residential and commercial real estate development in the Greater Toronto Area. They are looking to hire a new Project Accountant to the team and this is a great opportunity for someone currently working in development accounting. This is a role within a CPA-accredited training company so if growing your career beyond just Project Accounting and Accounts Payable is a motivation of yours, apply now!

Responsibilities:

• Create purchase orders and change orders within the accounting system using cost codes consistent with project budgets while complying to project specific workflows;

• Prepare invoice packages for draw packages;

• Review invoices, collect supporting backup, and facilitate approvals for the Development Department payment processing;

• Conduct vendor progress billing, hold back and job cost reconciliations on an ongoing basis;

• Generate variance reports to Project Managers and assist with quarterly project cost-to-complete reviews;

• Provide support with mailing/couriering cheques as needed and filing paid invoices promptly and accurately;

• Prepare project related accrual reports to support monthly draws for the Accounting Department;

Requirements:

• Degree or diploma

• Experience working in Accounts Payable within real estate development or construction

• Knowledge of accounting and finance principles and practices, and the analysis and reporting of financial-related reports

• Experience with Draws and/or large construction/consultant contracts

• Proficiency in MS Office, including Word, Excel and Outlook

• Ability to communicate effectively, both verbally and in writing

If you are interested in learning more about this opportunity, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Manager, Land Development Accounting

North York (In-office role)

$100k – $110k plus discretionary bonus and benefits

Our client, a leader in land development, is seeking a Manager, Land Development Accounting to join their team. The successful candidate will oversee financial operations for a diverse portfolio of land development projects, providing key insights and leadership.

Responsibilities:

• Oversee accounting and financial operations for assigned portfolios, including land purchase and sales, cost recoveries, trial balance reviews, account reconciliations, and job costing.

• Provide accurate and timely monthly, quarterly, and annual reporting, including variance and cost analysis for Senior Management and Project Managers.

• Prepare and maintain detailed project budgets in collaboration with Project Managers and the Finance Team, focusing on construction costs and fee analysis.

• Monitor and manage cash flow for development projects, including cash flow forecasting, funding draws, and loan utilization.

• Review invoices, manage change order processing, and oversee invoice coding.

• Prepare and reconcile internal and external loans, including interest calculations.

• Supervise and provide oversight to the land development accounting team.

• Assist in year-end financial statement preparation in compliance with accounting principles and audits.

• Document and maintain accurate financial transaction records.

• Lead ad hoc projects and analyses to support company objectives.

Requirements:

• CPA designation

• Bachelor’s degree in business or accounting.

• Several years of experience in full-cycle accounting within land development or property accounting.

• Proficiency in cash flow analysis, budgeting, and understanding joint business arrangements (e.g., JVs, partnerships).

• Strong problem-solving skills with attention to operational and financial impacts.

• Advanced proficiency in Microsoft Office, particularly Excel

If you are interested in applying for this opportunity, please email your resume to laikyn@winchesters.ca. Due to the high volume of applicants, only those selected for interviews will be contacted.

Junior Accountant
North York (In-office role)
$60k – $70k plus discretionary bonus and benefits

Our client, a leader in land development, is looking for a Junior Accountant to join their team. This role is ideal for someone highly motivated, detail-oriented, and ready to thrive in a fast-paced environment. The successful candidate will take on accounting tasks for a diverse portfolio of land development projects.

Responsibilities:

• Perform monthly bank reconciliations and manage accounts payable for multiple entities.

• Track and reconcile lot discharges, house closings, and loan balances with external statements.

• Set up and maintain accounts receivable invoices and process internal and external cash calls.

• Reconcile intercompany accounts and create/post journal entries.

• Prepare HST returns (monthly, quarterly, or annually).

• Manage and reconcile letters of credit for all projects.

• Maintain accounting records in compliance with Canadian GAAP and company policies.

• Support auditors with accurate and timely documentation.

• Participate in special projects and back charge processing.

Requirements:

• Bachelor’s degree in Business or Accounting; CPA designation or equivalent is an asset.

• 1-2+ years of experience in accounting

• Excellent communication skills and a collaborative team player.

If you are interested in applying for this opportunity, please email your resume to laikyn@winchesters.ca. Due to the high volume of applicants, only those selected for interviews will be contacted.

EVP, Finance & Administration
Toronto | In-office | Real Estate
$220,000-$240,000 base plus 30% bonus and future LTIP

We are recruiting an Executive Vice President, Finance & Administration for a growing real estate investment company in Toronto. This is a newly created role, reporting directly to the CEO, and will be a key player in shaping the company’s financial and operational strategy as it scales.

The company specializes in acquiring and managing properties across Canada and the U.S. With strong financial backing and a growing portfolio, they are now building out their internal finance and administrative functions. The EVP will be responsible for establishing financial infrastructure, implementing systems and processes, and transitioning away from a third-party service agreement. The role will also oversee financial reporting, budgeting, forecasting, tax, treasury, risk management, IT, HR, and office operations.

In the near term, priorities will include:

• Setting up financial systems and processes to support growth.

• Managing the transition away from a third-party finance provider before their contract ends in 2025.

• Refinancing a bridge loan as part of the company’s financial strategy.

• Building relationships with external advisors, auditors, and lenders to ensure compliance and efficiency.

As the company scales, the EVP will play a strategic role in:

• Supporting acquisitions and optimizing assets for long-term value.

• Developing and implementing key financial metrics and KPIs to guide decision-making.

• Providing financial leadership to the board and investors, ensuring transparency and strong governance.

• Building and leading a high-performing finance team to support the company’s growth.

Who We’re Looking For

The ideal candidate is a proven finance leader with experience in real estate, asset management, or other recurring revenue business models. They should have a trackrecord of scaling a finance function, leading financial strategy, and working closely with investors and boards. Strong analytical skills, business acumen, and the ability to balance strategic thinking with hands-on execution are essential.

Qualifications

• CPA designation required

• Experience in real estate, asset management, or private equity-backed companies is highly desirable.

• Strong background in financial reporting, FP&A, treasury, and tax.

• Experience with process automation and financial system implementation is a plus.

• Ability to work effectively in a fast-growing, entrepreneurial environment.

• Fluent French speakers will be prioritized.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Corporate Controller
Downtown Toronto, Ontario | hybrid
$130,000-$150,000 base plus bonus and benefits

Our client is a growing diversified real estate company in downtown Toronto, Ontario, Canada.

This established company has been in business for more than 20 years and continues to grow with a number of exciting projects coming up. The CFO is looking for a Corporate Controller to join the team working in the corporate office, located in Toronto, Ontario. The Corporate Controller will lead the corporate accounting and financial reporting functions of the department. You will manage the accounting and control functions and report results of operations ensuring compliance with IFRS standards.

In this role you will supervise an experienced team of 5 individuals, while having the full support of an excellent and experienced CFO. Accounting is not just seen as a back-office cost in this company, you are well-respected and lead on a number of special projects and initiatives. Ideally you will come with at least a few recent years in real estate and have supervisory experience.

Responsibilities

• Respond to all investor questions, information requests, ad hoc reporting requirements on a timely basis

• Oversee the preparation of quarterly financial statements and annual audited financial statements for each fund or segregated mandate

• Prepare quarterly cash flow updates for the funds and segregated mandates.

• Ensure development and construction budgets are updated quarterly within the accounting system along with approved PO, contracts and change orders

• Monthly, quarterly and annual corporate accounting and financial reporting

• Maintain internal controls over invoice entry, approval and ultimately payment to vendors.

• Review and comment on quarterly project cash flows providing insight into financial costs such as interest, insurance, property taxes, cash flows, etc.

• Prepare and present the annual budget for the management company

• Re-forecast the annual budget quarterly, investigate all actual to forecasted variances

• Prepare timely distributions to the Partners

• Manage and maintain the company’s fee schedule ensuring all fees are charged on a timely basis

• Manage a team of accountants and accounts payable coordinators

Requirements

• College diploma or University degree coupled with the CPA completed

• 8+ years of accounting experience

• Working knowledge and understanding of the real estate sector

• Working knowledge of inter-company accounting

• Excellent communication skills, both oral and written

• Ability to work effectively in a team environment as well as independently

• Hands-on approach to accounting and management

If you are interested in learning more about this opportunity, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

Financial Controller

$145,000 - $165,000 + excellent bonus and benefits 

North York, ON (On-site)

A well-established and growth-focused real estate development and investment firm is seeking a senior-level accounting and finance professional to join its leadership team. The role is instrumental in supporting the financial operations of large-scale commercial and residential development projects. This is a senior position, second only to the executive finance lead, and offers broad exposure to corporate finance, project accounting, investor relations, and strategic planning.

Key Responsibilities:

• Manage full-cycle accounting for assigned entities, including reconciliations, HST filings, and financial reporting.

• Review and oversee unit closings, including interim and final occupancy entries.

• Compare internal accounting records with third-party reports (e.g., cost consultants).

• Oversee the accounting functions of management companies, including expense tracking and credit card reconciliation.

• Lead and mentor a team of project accountants and senior project accountants.

• Standardize monthly financial reporting across all projects for consistency and accuracy.

• Review and approve monthly reconciliations, HST filings, and budget forecasts.

• Supervise month-end and year-end close processes and ensure timely financial reporting.

• Monitor project budgets and provide variance analysis.

• Collaborate with senior leadership to deliver financial insights that support operational and strategic goals.

• Coordinate and prepare financial documents for external accountants and audits.

• Maintain and improve internal controls over banking, wire transfers, and tax filings.

• Identify inefficiencies and develop internal policies to streamline processes.

• Lead improvements in reporting, budgeting, and internal workflows.

• Maximize utilization of Newstar and assess future system needs.

Qualifications

• CPA designation (CA, CGA, or equivalent) required.

• Minimum 3 years of experience in a supervisory accounting role, must be in real estate or property development.

• Experience using Newstar is mandatory

• Excellent communication, organizational, and analytical skills.

• High level of integrity, ownership mindset, and strong attention to detail.

• Proficiency in Microsoft Office, especially Excel.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Manager of Finance and Accounting

$130,000 – $140,000 base + large bonus 

5 days per week in office – Downtown Toronto

Our client, a premier Canadian private equity investment firm, is recruiting for a driven and solutions-oriented Manager of Finance. This is an exceptional opportunity to join a high-performing team in downtown Toronto that values integrity, transparency, and ownership.

The Role

Reporting directly to the Director of Finance, you will take ownership of the financial management for a specific portfolio of funds. This role offers a diverse mix of responsibilities, ranging from the preparation of consolidated financial statements and investor reporting to treasury management and debt compliance. You will work cross-functionally, partnering with asset management and investment teams to support transaction closings and strategic analysis. This position is ideal for a professional who thrives in a fast-paced environment and takes pride in delivering high-quality, accurate work.

Key Responsibilities

• Financial Reporting: Manage the monthly and quarterly reporting process, including the preparation of consolidated financial statements, investor summary reports, and real estate portfolio analysis.

• Annual Consolidation: Lead the annual consolidation of Fund financial results, including the preparation of year-end audit working papers and ASPE financial statements, while liaising with external auditors and tax teams.

• Budgeting & Forecasting: Manage the annual budget process and assist with ongoing financial planning.

• Investor Relations: Oversee investor-related activities, including the calculation and processing of capital calls and distributions, reviewing investor statements, and maintaining the integrity of the investor database.

• Treasury Management: Manage the treasury process by forecasting cash flows, managing borrowings, and accurately allocating debt and interest.

• Compliance: Prepare debt compliance packages and actively manage capital models to ensure Funds remain compliant with banking covenants.

• Operational Support: Assist asset management and investment teams with information requests, reviewing Statements of Adjustments (SOAs), and providing ad hoc analysis as required.

About You

• Undergraduate degree

• CPA completed.

• 4–5 years of experience in finance or accounting.

• Experience in the Real Estate industry is highly preferred.

• Strong working knowledge of financial statements and ASPE standards.

• Strong written and verbal communication skills, capable of dealing with internal and external stakeholders at all levels.

• A team player who is dedicated, organized, and capable of managing competing priorities under tight deadlines.

If you are interested in learning more about this opportunity, please apply now by sending your resume to eric@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Analyst, Finance

Toronto, ON (In office)

$100,000- $110,000 with excellent bonus and benefits

Our client, a well-established real estate investment and development company is seeking a Senior Financial Analyst to join its corporate team. This role supports the financial reporting and planning functions for a growing real estate portfolio. This is a great position for someone who wants to be exposed to a ton of unique responsibilities and quickly move up to the Manager level within 1-2 years.

Responsibilities:

• Review monthly financial packages from third-party operators, ensuring accuracy and completeness.

• Support investment onboarding and offboarding, including coordination with property managers and review of entity structures, closing statements, and related financial documentation.

• Lead process improvements related to intercompany reconciliations.

• Prepare and submit monthly and quarterly financial deliverables, including IFRS reporting packages, investment performance updates, and lender/co-investor reports.

• Manage internal controls and compliance activities, including SOX testing and external audits.

• Consolidate and analyze quarterly income statement reforecasts and contribute to annual budgeting and planning.

• Monitor liquidity and capital requirements, collaborating closely with portfolio management and capital markets teams.

• Support financing and refinancing initiatives.

• Ad hoc special projects

Qualifications:

• Bachelor's degree

• 3+ years of progressive experience in accounting

• Strong knowledge of IFRS accounting and financial consolidation is nice to have

• Exposure to real estate, private equity, or asset management is an asset.

• Excellent organizational, analytical, and communication skills.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Financial Reporting Manager

$115,000–$130,000 + bonus + great RRSP plan and excellent benefits

Downtown Toronto, ON | onsite

We are recruiting for a Financial Reporting Manager to join a highly respected real estate investment and asset management firm with a portfolio of prestigious assets in downtown North America. This is a fantastic opportunity for someone with a strong audit firm background or real estate private equity / asset management background — who wants to step into a high-profile, visible role working closely with the VP of Finance and senior leadership.

This position offers strong career development, exposure to investor relations, and the chance to work on a premier portfolio.

Responsibilities:

• Prepare and review monthly and quarterly IFRS-based financial forecasts

• Analyze cash flow projections for a range of properties

• Assist with annual business plans, budget packages, and valuation projections

• Review monthly co-ownership financials and support quarterly reporting cycles

• Develop management presentations and financial analysis for senior stakeholders

• Monitor and ensure compliance with loan covenants and reporting requirements

• Partner with asset management, leasing, marketing, and investor relations teams

• Support the month-end close process alongside the accounting team

• Lead or contribute to special projects and ad hoc financial analysis

Requirements:

• 3-5+ years of progressive experience in audit, accounting, reporting, finance, or FP&A

• Experience in real estate strongly preferred

• CPA designation is an asset or pursuing

• Strong communication, organization, and analytical abilities

• Comfortable working in a high-performance, fast-paced environment

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca.

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Senior Associate, Investments

$120,000 - $140,000 base + bonus and deal incentives 

Downtown Toronto, Ontario (4 days per week in office) 

Our client, a growing real estate equity investment firm located in Downtown Toronto, is recruiting for a highly analytical and driven Senior Associate, Investments. This is an outstanding opportunity for an investment professional to evaluate new opportunities and support the management of a diverse national portfolio of real estate developments. You will work closely with internal leadership and external partners including developers, consultants, and legal counsel across the full investment lifecycle.

In this role, you will play a key part in the firm's growth by leading financial underwriting, due diligence, and portfolio monitoring for premier real estate investments across Canada. You will prepare financial pro-formas, investment committee materials, and quarterly investor reports, while also assisting in the origination of new investment opportunities and expanding the firm's network of real estate professionals.

Key Responsibilities

• Lead the preparation of financial pro-formas and investment analyses for residential and commercial real estate developments and income-producing assets.

• Prepare financing packages, investment presentation materials, and materials for investment committee and board of directors' meetings.

• Perform ad hoc financial analysis, business planning, quarterly project updates, and investor reporting for the current portfolio.

• Support and coordinate due diligence and transaction execution for new investments, reviewing development budgets, schedules, and market reports.

• Collaborate effectively with third-party consultants, internal stakeholders, and legal counsel to evaluate and advance investment opportunities.

• Assist in originating new investment opportunities and growing the firm’s network of partners.

Requirements

• Bachelor's degree in Business, Finance, Real Estate, or a related field; CFA designation or progression toward a CFA is preferred.

• 4+ years of relevant experience in real estate investments, development, private equity, or a related field.

• Strong financial modeling and analytical capabilities, with advanced proficiency in Microsoft Excel.

• Excellent communication and interpersonal skills, with the proven ability to lead projects and collaborate with external advisors.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.

Director, Finance

$160,000 - $170,000 base + variable discretionary bonus 

Toronto, Ontario 

Our client, a leading Canadian private equity investment business located in downtown Toronto, Ontario, is recruiting for a solutions-oriented and accountable Director of Accounting. This is an great opportunity for a dedicated finance professional with strong critical thinking skills who wants to play a hands-on role in overseeing fund operations, reporting, and team mentorship. You will work closely with the CFO, the FP&A team, and all levels of the organization - to ensure accurate financial forecasting and compliance.

In this role, you will oversee the preparation of monthly, quarterly, and annual reporting deliverables for a portfolio of funds while ensuring adherence to ASPE. You will manage quarterly board reporting, oversee the annual budget process, and act as the key liaison for the annual audit. Additionally, you will lead and mentor a team of four direct reports and manage critical investor transactions, including capital calls and distributions.

Key Responsibilities

• Oversee the preparation of monthly, quarterly, and annual reporting deliverables, ensuring accuracy, deadline adherence, and ASPE compliance.

• Review monthly fund forecasts to ensure covenant adherence, adequate liquidity, and accurate tracking of acquisitions and dispositions.

• Manage the quarterly board reporting process and oversee compliance reporting to lenders.

• Lead the annual budget process by reviewing the accuracy and reasonability of assumptions.

• Act as the primary liaison for the annual audit process.

• Direct investor transactions by overseeing the preparation of capital call, capital return, preferred return, and gain distribution files.

• Respond promptly and professionally to all investor inquiries.

• Provide leadership, mentorship, and guidance to a team of four direct reports.

Requirements

• Undergraduate degree in finance or business.

• CPA designation is required.

• 8+ years of experience in a business or finance role.

• Previous experience in the real estate industry is considered an asset.

• Advanced proficiency in EXCEL and strong familiarity with Word and PowerPoint.

• Highest ethical standards with displayed professional and personal integrity.

If you are interested in learning more about this opportunity, please apply now. Unfortunately, due to the high volume of applicants, only those individuals chosen for interview will be contacted.

If you are interested in learning more about this opportunity, please apply now by sending your resume to elan@winchesters.ca

Unfortunately, due to the high volume of applicants, only those selected for an interview will be contacted.